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CA1194472A - Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group - Google Patents

Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group

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Publication number
CA1194472A
CA1194472A CA000408056A CA408056A CA1194472A CA 1194472 A CA1194472 A CA 1194472A CA 000408056 A CA000408056 A CA 000408056A CA 408056 A CA408056 A CA 408056A CA 1194472 A CA1194472 A CA 1194472A
Authority
CA
Canada
Prior art keywords
process according
group
alkyl
formula
carbon atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
CA000408056A
Other languages
French (fr)
Inventor
El-Ahmadi I. Heiba
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience SA
Original Assignee
Rhone Poulenc Agrochimie SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhone Poulenc Agrochimie SA filed Critical Rhone Poulenc Agrochimie SA
Application granted granted Critical
Publication of CA1194472A publication Critical patent/CA1194472A/en
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N1/00—Preservation of bodies of humans or animals, or parts thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C301/00—Esters of sulfurous acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/51—Y being a hydrogen or a carbon atom
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
    • C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/60—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/33—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
    • C07C323/35—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group
    • C07C323/36—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
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    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/40—Y being a hydrogen or a carbon atom
    • C07C323/41—Y being a hydrogen or an acyclic carbon atom
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    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom
    • C07C323/44—X or Y being nitrogen atoms
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    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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    • C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
    • C07C323/65—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfone or sulfoxide groups bound to the carbon skeleton
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    • C07C323/67—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfonamide groups, bound to the carbon skeleton
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    • C07C331/02—Thiocyanates
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    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/275—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings having all ether-oxygen atoms bound to carbon atoms of six-membered aromatic rings
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
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    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
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    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
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    • C07F9/08—Esters of oxyacids of phosphorus
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
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    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
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    • A—HUMAN NECESSITIES
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Abstract

ABSTRACT

Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group, by reacting an acid halide with a sulphonamide in the absence of an acid acceptor and with elimination of hydrohalic acid in the gaseous form.

Description

The present invention relates to an improved process for the preparation of certain phenoxybenzoie acid deriva-tives containlng a sulphonamide group, ~7hieh have herbieidal properties.
Herbieidal derivatives of phenoxybenzole aeids eontaining a sulphonamide group are known from European Paten-t Applieations 3,416 and 23,392 published on 8th Au~ust, 1979 and A-th Fe~ruary, 1981, respeetively.
These pa-tent applieations disclose products of the formula:

C B R

D ~ ~ ~ ~ A (II~

E F

and their salts, in whieh formula:
A is hydrogen, fluorine, chlorine, bromine, iodine, a n.i-tro groupr -N=NCF3, PO3H2 or an alkyl ester -thereof having 1 to 4 carbon atoms, NH2, NHOH, N2, a carboxy group or one of its funetional derivatives, a monoalkylamino or dialkylam-no group, a group NH~CO-R , in whieh R is an alkyl, alkoxy, monoalkyl.amino or dialkylamino radieal, an alkyl group, trialkylammonio, NHSO2R , in which R is an alkyl or phenyl radical, NHCONHSO2R , in which R is as hereinbefore defined; alkylthio, alkylsulphinyl, alkyl-sul.phonyl, dialkylsulphonio, cyano-mab/lf`rl sulphonyl, hydroxy, alkanoyloxy, alkoxy, alkoxy substitu-ted by an alkoxycarbonyl group, SH, nitroso, -SCN, azide, CF3, -N=N-P(OCH3)2 or acyl, B is hydrogen, flllorirle, chlorine, bromine, iodine, an alkyl, alkoxy, alkylsulphinyl or alkylsulphonyl group, CF3, NO2, CN~ NH~, NHCOR , in which R is as :hereinbefore defined, or CO~H2, C is hydrogen, fluorine, chlorine, bromine, iodine or an alkyl or dialkylamino group;
D is fluorine, chlorine, bromine, iodine or an alkylthio, alkylsulphinyl, alkylsulphonyl, alkyl, halogeno-alkyl, preferably CF3, sulphamoyl, formyl, alkylcarbonyl, CN or dimethylamino group, E is hydrogen, fluorine, chlorine, bromine, iodine, an alkyl, alkoxy, alkylsulphinyl or alkylsulphonyl group, CN, halogenoalkyl, preferably CF3, NH2, CONH2 or N~I-CO-R , wherein R is as hereinbefore defined, F is as hereinbefore defined for B, and R is a group -CO~(R )SO2R , in which:
R4 is hydrogen or an alkyl group having 1 to 4 carbon atoms, and R is a phenyl, pyridyl or thienyl group optionally substituted ~y one or more halogen atoms, ~lkyl groups or nitro groups, an alkenyl or alkynyl radical having
2 to 4 carbon atoms, or an alkyl radical having 1 to 4 carbon atoms, which is optionally substituted by one or more fluorine, chlorine, bromine or iodine atoms) preferably CF3, or by one or more of the following substituents: carboxy, alkoxycarbonyl ha-~ing 2 to 5 carbon atoms, alkylcarbonyl having 2 to 5 carbon atoms, monoalkyl-carbamoyl or dialkylcarbamoyl, in which the alkyl groups have from 1 to 4 carbon atoms, alko~y having 1 to h carbon atoms, alkylthio, alkylsulphinyl, alkylsulphonyl, each having from 1 to 4 carbon atoms, alkylcarbonyloxy having 2 to 5 car~on atoms, alkylcarbonylamino having 2 to 5 carbon atoms, or cyano.
In t~e above definitions, where reference is made to alkyl radicals or radicals containing one or more alkyl ~roups, for example mono- and di-alkylamino, or alkoxy, the alkyl radical may be for example a lower alkyl radical having for example 1 to 6 carbon atoms.
In the known processes, the products of the -formula (I) are prepared by reacting an intermediate acid halide of the formula-C B COX

D ~ -0- ~ A (II) E F

wherein X is chlorine, bromine or iodine and A, B, C, D, E
and F are as hereinbefore defined, with a sulphonamide of the formula: 3 2 2 (III) wherein R3 is as hereir~efore defined, at from 25 to 140C, in the presence of an acid accepto.r, in particular a tertiary amine, such as ~,N-dimethylaniline or pyridine, an alkali metal carbonate, such as anhydrous potassium c~rbonate, or an alkali metal fluoride, such as caesium fluorideO

~ le compounds of formula (I) in which R4 is hydrogen can be alkylated in a known manner, e.y. by reaction with a diazoalkane having 1 to 4 carbon atoms, so as to give the cc~rresponding products in which R4 is an alkyl group ha~ing 1 to 4 carkon atoms.
The compounds of formula I in which, for exarnple, R4 is a hydrogen atom are acids and form salts with bases:
such compounds may be converted in known manner into their salts.
This process for the condensation of the products of formulae ~II) and (III) has a number of disadvantages:
the yields are mediocre (e~g. it is possible to calculate a yield of 27% for Example 14 of E-.lropean Patent Application 23,392 and of 9.5% for Example 34)O It is now considered that it is the presence of the acid acceptor which lowers the yield by promoting a diacylation reaction. Fur-thermore, the use of an acid acceptor makes the final products more difficult and more expensive to isolate and purify. An object of the invention is to overcome these disadvantages.
The process accordlng to the invantlon comprises reacting an acid halide of formula II wherein X, A, B, C, D, E and F are as hereinbefore defined wi~h a sulphonamide of formula (III), wherein R i,s as hereinbefore defined, in -the absence of an acid acceptor and at a temperature at which the gaseous hydrogen halide (HCl, HBr or HI) formed during the reaction is eliminated from the reaction medium, as it is formed, the reaction temperature being be].ow the decomposition temperature of the product of fo~mula (I) ~i.e~ the xeaction i5 carried out at a temperature at which appreciable decomposition of the xeaction prvduct of the formula (I) does not occur) and optionally converting in known manner a compound thus obtained into a sal-t thereof or converting in known manner a compound thus obtained wherein R4 represents a hydrogen atom into a corresponding compound wherein R4 represents an alkyl group having 1 to carbon atoms~
By virtue of the process according -to the invention, substantially higher yields of sulphonamide derivatives of phenoxybenzoic acids can be obtained, eOg.
yields of at least about 30% and frequently of at least about 50%, and with a much simpler me-thod of recovering and purifying the final product than the methods of the kn~wn processes.
It is pre-ferred to use an acid halide (preferably the chloride) of formllla (II) in which A is the group ~2 or a fluorine, chlorine, bromine or iodine atom, B is a halogen (preferably chlorine) atom, C, E and F are hydrogen and D is the group CF3O It is also prefexred to use sulphon-amides of formula (III) in which R3 is an alkyl group, especially CH3l or a group CF3~
The temperature at which the process of the invention can be carried out depends, in particular, on whether either the acid halide of the formula (II~ or the ~ 6 sulphonamide of the formula (III) is in large excess, or on whether or not a solvent having catalytic properties is usedO
~he reaction may be carried out in the presence of an excess of acid halide of formula (II). If the acid halide ~II) is in large excess, i.eO the molar ratio (II)/
(III) is from about 1.5 to 5, as is preferred, the acid halide (II) can serve as a solvent for the reaction and the reaction temperature can be from 80 to 200C, but it is then preferably from 90 to 160C.
~he unreacted acid halide (II) can be recovered from the reaction medium by washing with an inert solvent, such as a hydrocarbon, in particular pentane, hexane, heptane, cyclopentane, cyclohexane, cycloheptane, benzene, toluene or ~ylene, a halogenated hydrocarbon, in particular chlorobenzenes, CS2, tetrahydrofuran, dioxane and the like~
~hen an excess of sulphonamide is used, for example when the molar ratio of the compounds (III)/(II) is f.rom 1.5 to 5, the reaction temperature is then generally from 90 to 200C and preferably from 140 to 160C~ In any case, it mu~st be at least sufficient to melt the reaction medium.
The excess sulphonamide (III) can be recovered from the reaction medium by washing with water or another inert solvent for this reactant ~III)~
~he reactants can also be dissolved in an inert solvent havi.ng a boiling point above the reaction temperature, e.g. a chlorinated or non-chlorinated liquid hydrocarbon, such as benzene, toluene, xylenes, mixtures of xylenes or ~umene, the maximum reaction temperature is advantageously slightly below the boiliny point of the solvent, Thus, in the case of cumene, which boils at about 153C, the reaction i5 preferably carried out at from 130 to 150C. me use of an inert solvent has the practical advantage of permitting better heat transfer in an in~ustrial-scale process, it also makes it possible to avoid local overheating of the reaction mediumO
According to another feature of the inventionl a solvent is used which catalyses the reaction of the acid halide (II) with the sulphonamide (III3 to give the phenoxy-benzoylsulphonamide ~ Dimethylformamide (DMF, which boils at about 154C) and dimethylacetamide (DMAC, which boils at about 164C) are particu~arly advantageous in this respect, and their use makes it possible to use relatively low temperatures, e.g. from 80 to 120C, preferably from 90 -to 110C, or higher temperatures slightly below the boiling point of these solvents; the reaction rate is then more rapid. It is especially preferred to carry out the reaction at a te~perature from 80C to -the boiling point of the solvent, preferably at a temperature above 90Co The following Examples illustrate the present inventionO

E~ample 1 Methanesulphonamide (2 g, On021 mol) is mixed with 5-[2'-chloro-4'~(trifluoromethyl)-p~enoxy]-2-nitro-benzoyl ~hloride (3.8 g; 0.01 mol). The mix-ture is heated for 20 minutes at 150C. The hydrochloric acid is released from the reaction medium as it is formed. ~ne medium is cooled to give a black oil, which is dissolved in aque~us sodium hydroxide solution; the solution is filtered and the filtrate is acidified with dilute HCl, which precipitates the product of the foxmula (IV~. ~his gave, with a yield of 71%, a product (3~1 g) meltiny at 195-197C and having an in~ra-red absorption band at 1,692 cm 1 (C=0 group~ This product has the ~ormula:

Cl ~ CO~NH-SO2-CH3 ~< /~
3 ~ ~ NO2 (IV) Example 2 Example 1 is repeated, but 250 g of acid chloride and 130 g of me-thanesulphonamide are used. The reaction product is isolated directly after the mixture has cooled~
by recrystallisation from isopropanol. This gives a yield of 64% (785 g~ of the product of the formula (IVl.
The s-tructure of this product is confirmed by infra-red (absorp-tion band at 1,692 cm ) and by nuclear magne-tic resonance (singlet at 3,5 ppm; multiplet at 8~07 ppm).
When applying the process of thi.s example of European Patent Application 23,392, using pyridine as an acid acceptor, -the yield was only 25%.

_ 9 _ mab/~

Claims (20)

The embodiments of the invention, in which an exclusive privilege or property is claimed, are defined as follows:
1. A process for the preparation of a phenoxybenzoic acid derivative containing a sulphonamide group, of the formula:

(I) and its salts, in which formula:
A is hydrogen, fluorine, chlorine, bromine, io-dine, a nitro group, -N=NCF3, PO3H2 or an alkyl ester thereof having 1 to 4 carbon atoms, NH2, NHOH, , a carboxy group or one of its functional derivatives, a monoalkyl-amino or dialkylamino group, a group NH-CO-R1, in which R1 is an alkyl, alkoxy, monoalkylamino or dialkylamino radical, an alkyl group, trialkylammonio, NHSO2R2, in which R2 is an alkyl or phenyl radical, NHCONHSO2R2, in which R2 is as hereinbefore defined, alkylthio, alkylsulphinyl, alkylsulphonyl, dialkylsulphonio, cyano-sulphonyl, hydroxy, alkanoyloxy, alkoxy, alkoxy substi-tuted by an alkoxycarbonyl group, SH, nitroso, -SCN, azide, CF3, or acyl;

B is hydrogen, fluorine, chlorine, bromine, io-dine, an alkyl, alkoxy, alkylsulphinyl or alkylsulphonyl group, CF3, NO2, CN, NH2, NHCOR1, in which R1 is as herein-before defined, or CONH2;

C is hydrogen, fluorine, chlorine, bromine, iodine or an alkyl or dialkylamino group;
D is fluorine, chlorine, bromine, iodine or an alkylthio, alkylsulphinyl, alkylsulphonyl, alkyl, halogeno-alkyl, sulphamoyl, formyl, alkylcarbonyl, CN or dimethyl-amino group, E is hydrogen, fluorine, chlorine, bromine, iodine, an alkyl, alkoxy, alkylsulphinyl or alkylsulphonyl group, CN, halogenoalkyl, NH2, CONH2 or NH-CO-R1, wherein R1 is as hereinbefore defined;
F is as hereinbefore defined for B, and R is a group -CON(R4)SO2R3, in which:
R4 is hydrogen or an alkyl group having 1 to 4 carbon atoms, and R3 is a phenyl, pyridyl or thienyl group optionally substituted by one or more halogen atoms, alkyl groups or nitro groups, an alkenyl or alkynyl radical having 2 to 4 carbon atoms, or an alkyl radical having 1 to 4 carbon atoms, which is optionally substituted by one or more fluorine, chlorine, bromine or iodine atoms, or by one or more of the following substituents: carboxy, alkoxycarbonyl having 2 to 5 carbon atoms, alkylcarbonyl having 2 to 5 carbon atoms, monoalkylcarbamoyl or dialkylcarbamoyl, in which the alkyl groups have from 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio, alkylsulphinyl, alkylsulphonyl, each having from 1 to 4 carbon atoms, alkylcarbonyloxy having 2 to 5 carbon atoms, alkyl-carbonylamino having 2 to 5 carbon atoms, or cyano, which process comprises reacting an acid halide of the formula:

(II) wherein X is a chlorine, bromine or iodine atom and A, B, C, D, E and F are as hereinbefore defined, with a sulphon-amide of the formula:
R3SO2NH2 (III) wherein R3 is as hereinbefore defined, in the absence of an acid acceptor and at a temperature at which the gaseous hydrogen halide formed during the reaction is eliminated from the reaction medium as it is formed, the reaction temperature being below the decomposition temperature of the product of formula (I) and optionally converting in known manner a compound thus obtained into a salt thereof or converting in known manner a compound thus obtained wherein R4 represents a hydrogen atom into a corresponding compound wherein R4 represents an alkyl group having 1 to 4 carbon atoms.
2. A process according to claim 1, wherein the reaction is carried out in the presence of an excess of acid halide of formula (II).
3. A process according to claim 2, wherein the molar ratio of acid halide of formula (III) to sulphonamide of formula (III) is from 1.5 to 5.
4. A process according to claim 2, wherein the reaction temperature is from 80 to 200°C,
5. A process according to claim 4 in which the temperature is from 90 to 160°C.
6. A process according to claim l, wherein the reaction is carried out in the presence of an excess of sulphonamide.
7. A process according to claim 6, wherein the molar ratio of sulphonamide of formula (III) to acid halide of formula (II) is from 1.5 to 5.
8. A process according to claim 6 or 7, wherein the reaction temperature is from 90 to 200°C.
9. A process according to claim 7 in which the temperature is from 140 to 160°C.
10. A process according to claim 1, wherein the reaction is carried out in the presence of a solvent having a boiling point above the reaction temperature.
11. A process according to claim 10, wherein the solvent is a chlorinated or non-chlorinated liquid hydrocarbon.
12. A process according to claim 11, wherein the solvent is cumene and wherein the reaction temperature is from 130 to 150°C.
13. A process according to claim 1, wherein the reaction is carried out in a solvent which catalyses the reaction of the acid halide of formula II and the sulphonamide of formula III.
14. A process according to claim 13, wherein the solvent is dimethylformamide or dimethylacetamide and the reaction temperature is from 80°C to the boiling point of the solvent.
15. A process according to claim 14, wherein the temperature is above 90°C.
16. A process according to claim 1 wherein, in formulae (II) and (III), B is halogen, X is chlorine, A is the group NO2 or a fluorine, chlorine, bromine or iodine atom, C, E, and F are hydrogen and D is CF3.
17. A process according to claim 1 wherein, in formulae (I) and (II), B and X are chlorine, A is chlorine or NO2, C, E, and F are hydrogen and D is CF3.
18 A process according to claim 1, wherein in the sulphonamide of formula III, R3 is an alkyl or CF3 group.
19. A process according to claim 18, wherein R3 is methyl.
20. A process according to claim 1 wherein is reacted with CH3-SO2-NH2.
CA000408056A 1981-07-27 1982-07-26 Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group Expired CA1194472A (en)

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