CN114933587A - Preparation method of trifloxysulfuron sodium salt - Google Patents
Preparation method of trifloxysulfuron sodium salt Download PDFInfo
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- CN114933587A CN114933587A CN202210465184.3A CN202210465184A CN114933587A CN 114933587 A CN114933587 A CN 114933587A CN 202210465184 A CN202210465184 A CN 202210465184A CN 114933587 A CN114933587 A CN 114933587A
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- Prior art keywords
- sodium salt
- reaction
- flonicarbazem
- producing
- trifloxysulfuron
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- 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.)
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- RRCWSLBKLVBFQD-UHFFFAOYSA-N 4-chloro-1-(2-methylpropyl)imidazo[4,5-c]quinoline Chemical class C1=CC=CC2=C3N(CC(C)C)C=NC3=C(Cl)N=C21 RRCWSLBKLVBFQD-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 8
- PEXWMSDUWGUEPX-UHFFFAOYSA-N 3-(2,2,2-trifluoroethoxy)pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=NC=CC=C1OCC(F)(F)F PEXWMSDUWGUEPX-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 6
- MESPVSMSORHLAX-UHFFFAOYSA-N phenyl n-(4,6-dimethoxypyrimidin-2-yl)carbamate Chemical compound COC1=CC(OC)=NC(NC(=O)OC=2C=CC=CC=2)=N1 MESPVSMSORHLAX-UHFFFAOYSA-N 0.000 claims abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000000967 suction filtration Methods 0.000 claims description 4
- 238000005580 one pot reaction Methods 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- -1 4, 6-dimethoxy-2-pyrimidinyl Chemical group 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 2
- OUHIBFVOENMCGO-UHFFFAOYSA-N 4-aminobenzenesulfonamide;pyridine Chemical compound C1=CC=NC=C1.NC1=CC=C(S(N)(=O)=O)C=C1 OUHIBFVOENMCGO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KKDWOCZHGIMIIF-UHFFFAOYSA-N N=C=O.C1=CN=CN=C1 Chemical compound N=C=O.C1=CN=CN=C1 KKDWOCZHGIMIIF-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- AIMMSOZBPYFASU-UHFFFAOYSA-N n-(4,6-dimethoxypyrimidin-2-yl)-n'-[3-(2,2,2-trifluoroethoxy)pyridin-1-ium-2-yl]sulfonylcarbamimidate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)OCC(F)(F)F)=N1 AIMMSOZBPYFASU-UHFFFAOYSA-N 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- QQDJRDGPOLDACD-UHFFFAOYSA-N sodium pyridin-2-ylsulfonylazanide Chemical compound [Na+].N1=C(C=CC=C1)S(=O)(=O)[NH-] QQDJRDGPOLDACD-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BNOVYBVKWYHEMQ-UHFFFAOYSA-N (4,6-dimethoxypyrimidin-2-yl)urea Chemical compound COC1=CC(OC)=NC(NC(N)=O)=N1 BNOVYBVKWYHEMQ-UHFFFAOYSA-N 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000234646 Cyperaceae Species 0.000 description 1
- 244000075634 Cyperus rotundus Species 0.000 description 1
- 235000016854 Cyperus rotundus Nutrition 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- IAUBZYYUBMBVPI-UHFFFAOYSA-N pyridine;sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O.C1=CC=NC=C1 IAUBZYYUBMBVPI-UHFFFAOYSA-N 0.000 description 1
- ZENDWEPAVHORFD-UHFFFAOYSA-N pyrimidine;urea Chemical compound NC(N)=O.C1=CN=CN=C1 ZENDWEPAVHORFD-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention discloses a preparation method of trifloxysulfuron sodium salt, which comprises the step of reacting 3- (2,2, 2-trifluoroethoxy) -2-pyridine sulfonamide, 4, 6-dimethoxy-2- (phenoxycarbonyl) aminopyrimidine and sodium hydroxide aqueous solution in an organic solvent in one step to obtain the trifloxysulfuron sodium salt. The method disclosed by the invention is short in reaction step, simple in operation, low in production cost, high in yield and suitable for industrial mass production.
Description
Technical Field
The invention belongs to the technical field of herbicide preparation, and particularly relates to a preparation method of trifloxysulfuron sodium.
Background
The trifloxysulfuron sodium salt is a sulfonylurea herbicide developed by the Profenoda corporation, and has the chemical name: n- [ (4, 6-dimethoxy-2-pyrimidinyl) carbamoyl ] -3- (2,2, 2-trifluoroethoxy) -pyridine-2-sulfamoyl sodium salt. After the trifloxysulfuron sodium salt is applied, the trifloxysulfuron sodium salt can be absorbed by roots, stems and leaves of weeds, the plants are suffered from damage and show growth point necrosis and leaf vein chlorosis, and finally the whole plants die due to withering, so that the trifloxysulfuron sodium salt is used for preventing and removing most of broadleaf weeds and part of gramineous weeds in cotton fields and sugarcane fields, and has special effects on cyperaceae weeds and cyperus rotundus.
The prior art discloses a preparation method of trifloxysulfuron sodium salt, which comprises the following steps:
firstly, 4, 6-dimethoxypyrimidine-2-isocyanate (hereinafter referred to as pyrimidine isocyanate) is used as a starting material, and is reacted with ammonia gas in dioxane to obtain 2-aminocarbonylamino-4, 6-dimethoxypyrimidine (hereinafter referred to as pyrimidine urea), then is reacted with sodium hydride in tetrahydrofuran to obtain pyrimidine urea sodium salt, and is reacted with 3- (2-trifluoroethoxy) pyridine-2-sulfonyl chloride (hereinafter referred to as pyridine sulfonyl chloride) to obtain trifloxysulfuron sodium salt [ see example H2 of Japanese patent document JPH11140081A ].
The specific synthetic route is as follows:
the method has the following defects: the reaction steps are longer, the reaction conditions are harsher, the operation is more complex, particularly, the yield is lower, and the last two steps are only 59 percent, so that the method is not suitable for industrial mass production.
Secondly, 4, 6-dimethoxypyrimidine-2-isocyanate (hereinafter referred to as pyrimidine isocyanate) is used as a starting material, and the starting material is directly reacted with 3- (2-trifluoroethoxy) pyridine-2-sulfonamide sodium salt (hereinafter referred to as pyridine sulfonamide sodium salt) in dioxane or tetrahydrofuran to obtain trifloxysulfuron sodium salt [ see example H1 of Japanese patent document JPH11140081A ].
The specific synthetic route is as follows:
the method has the following defects: the pyridine sulfonamide sodium salt used as the raw material has limited sources and higher price, so the production cost is lower and the method is not suitable for industrialized mass production.
Disclosure of Invention
The invention aims to solve the problems and provides a preparation method of trifloxysulfuron sodium salt, which has the advantages of short reaction steps, simple operation, low production cost and high yield.
The technical scheme for realizing the purpose of the invention is as follows: a method for preparing trifloxysulfuron sodium salt, characterized in that: the trifloxysulfuron sodium salt is obtained by one-step reaction of 3- (2,2, 2-trifluoroethoxy) -2-pyridinesulfonamide [ hereinafter referred to as pyridinesulfonamide ] with 4, 6-dimethoxy-2- (phenoxycarbonyl) aminopyrimidine [ hereinafter referred to as pyrimidine phenyl ester ] and sodium hydroxide aqueous solution in an organic solvent.
The specific synthetic route is as follows:
the molar ratio of the pyridine sulfonamide to the pyrimidine phenyl ester is 1: 1-1: 1.2, and preferably 1: 1.
The molar ratio of the pyridine sulfonamide to the sodium hydroxide is 1: 1-1: 2, and preferably 1: 1-1: 1.1.
The reaction temperature is 0-50 ℃, and preferably 5-10 ℃.
The reaction time is 2-10 h, preferably 6 h.
The organic solvent is one of acetonitrile, dioxane, acetone, N-dimethylformamide and methyl isobutyl ketone, and is preferably acetonitrile or dioxane.
After the reaction, post-treatment is also included; and the post-treatment comprises suction filtration, rinsing and drying.
The rinsing solvent is the same as the reaction organic solvent in kind; the drying temperature is 100 ℃.
The invention has the following positive effects: the method adopts the one-step reaction of the 3- (2,2, 2-trifluoroethoxy) -2-pyridine sulfonamide, the 4, 6-dimethoxy-2- (phenoxycarbonyl) aminopyrimidine and the sodium hydroxide aqueous solution in the organic solvent to obtain the trifloxysulfuron sodium salt, and has the advantages of short reaction step, simple operation, low production cost and high yield, thereby being suitable for industrial mass production.
Detailed Description
(example 1)
The preparation method of trifloxysulfuron sodium salt of this example is as follows:
adding 84.0g (0.328 mol) of pyridine sulfanilamide, 90.2g (0.328 mol) of pyrimidine phenyl ester and 520mL of acetonitrile into a 1000mL four-neck flask in sequence, stirring and dissolving, cooling to 5 ℃, dropwise adding 28.8g (0.36 mol) of 50wt% sodium hydroxide aqueous solution for about 1h, and then carrying out heat preservation reaction for 6h at the temperature of 5-10 ℃.
After the reaction, the reaction solution was filtered, rinsed with a small amount of acetonitrile, and dried at 100 ℃ to obtain 138.5g of white crystal trifloxysulfuron sodium salt with a yield of 92.0% and a purity of 99.2% (HPLC).
1 H NMR（400MHz，Chloroform-d）δ：7.713～7.723(d,1H,J=4,CH)，7.685(s,1H,CH)，7.435～7.456(d,1H,J=8.4,CH)，7.085～7.116(m,1H,CH)，5.583(s,1H,NH)，4.588～4.652(m,2H,CH 2 )，3.797(s,6H,CH 3 )。
(example 2)
The preparation method of trifloxysulfuron sodium salt of this example is as follows:
76.8g (0.3 mol) of pyridine sulfanilamide, 82.5g (0.3 mol) of phenyl pyrimidine and 500mL of dioxane are sequentially added into a 1000mL four-neck flask, stirred and dissolved, cooled to 5 ℃, dropwise added with 24.0g (0.3 mol) of 50wt% sodium hydroxide aqueous solution for about 1h, and then subjected to heat preservation reaction at the temperature of 5-10 ℃ for 6 h.
After the reaction, suction filtration was carried out, rinsing was carried out with a small amount of dioxane, and drying was carried out at 100 ℃ to obtain 125.3g of white crystal trifloxysulfuron sodium salt, with a yield of 91.0% and a purity of 98.7% (HPLC).
Comparative example 1
The preparation method of the trifloxysulfuron sodium salt of this comparative example is as follows:
76.8g (0.3 mol) of pyridine sulfonamide, 82.5g (0.3 mol) of phenylpyrimidine, 45.6g (0.3 mol) of DBU and 500mL of acetonitrile were sequentially added to a 1000mL four-necked flask and reacted at room temperature for 2 hours.
After the reaction, the solvent was evaporated under reduced pressure, hydrochloric acid and water were added to the residue to acidify, a white solid was precipitated, filtered, rinsed with a small amount of water, and dried to obtain 124.6g of trifloxysulfuron with a yield of 95.0% and a purity of 97.5%.
② 124.6g (0.285 mol) of trifloxysulfuron obtained in the step I and 300mL of methanol are added into a 1000mL four-mouth bottle, then 51.3g (containing 0.285mol of sodium methoxide) of 30wt% sodium methoxide/methanol solution is dripped, and the mixture is heated to reflux reaction for 30 min.
After the reaction is finished, most of the solvent is evaporated, the temperature is cooled to 0-5 ℃ to obtain viscous solid, and the viscous solid is subjected to suction filtration and drying to obtain 102.0g of trifloxysulfuron sodium salt, wherein the yield is 77.9% and the purity is 97.2%.
The yield of the two steps is 74.1 percent based on the pyridine sulfonamide.
Claims (8)
1. A preparation method of trifloxysulfuron sodium salt is characterized in that: the trifloxysulfuron sodium salt is obtained by one-step reaction of 3- (2,2, 2-trifluoroethoxy) -2-pyridine sulfonamide, 4, 6-dimethoxy-2- (phenoxycarbonyl) aminopyrimidine and sodium hydroxide aqueous solution in an organic solvent.
2. The method for producing flonicarbazem sodium salt according to claim 1, characterized in that: the molar ratio of the 3- (2,2, 2-trifluoroethoxy) -2-pyridine sulfonamide to the 4, 6-dimethoxy-2- (phenoxycarbonyl) aminopyrimidine is 1: 1-1: 1.2.
3. The method for producing flonicarbazem sodium salt according to claim 1, characterized in that: the molar ratio of the 3- (2,2, 2-trifluoroethoxy) -2-pyridine sulfonamide to the sodium hydroxide is 1: 1-1: 2.
4. The method for producing flonicarbazem sodium salt according to claim 1, characterized in that: the reaction temperature is 0-50 ℃, and the reaction time is 2-10 h.
5. The method for producing flonicarbazem sodium salt according to claim 1, characterized in that: the organic solvent is one of acetonitrile, dioxane, acetone, N-dimethylformamide and methyl isobutyl ketone.
6. The process for producing flonicarbazem sodium salt according to claim 5, characterized in that: the organic solvent is acetonitrile or dioxane.
7. The method for producing flonicarbazem sodium salt according to claim 1, characterized in that: after the reaction, post-treatment is also included; and the post-treatment comprises suction filtration, rinsing and drying.
8. The method for producing flonicarbazem sodium salt according to claim 7, characterized in that: the rinsing solvent is the same as the reaction organic solvent in kind; the drying temperature is 100 ℃.
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|---|---|---|---|
| CN202210465184.3A CN114933587A (en) | 2022-04-29 | 2022-04-29 | Preparation method of trifloxysulfuron sodium salt |
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| CN202210465184.3A CN114933587A (en) | 2022-04-29 | 2022-04-29 | Preparation method of trifloxysulfuron sodium salt |
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| CN202210465184.3A Pending CN114933587A (en) | 2022-04-29 | 2022-04-29 | Preparation method of trifloxysulfuron sodium salt |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992016522A1 (en) * | 1991-03-25 | 1992-10-01 | Ciba-Geigy Ag | Novel sulfonylureas |
| CN1404360A (en) * | 2000-02-10 | 2003-03-19 | 辛根塔参与股份公司 | Novel use of herbicides |
| CN101993431A (en) * | 2009-08-25 | 2011-03-30 | 徐波勇 | Method for synthesizing trifloxysulfuron |
-
2022
- 2022-04-29 CN CN202210465184.3A patent/CN114933587A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992016522A1 (en) * | 1991-03-25 | 1992-10-01 | Ciba-Geigy Ag | Novel sulfonylureas |
| CN1404360A (en) * | 2000-02-10 | 2003-03-19 | 辛根塔参与股份公司 | Novel use of herbicides |
| CN101993431A (en) * | 2009-08-25 | 2011-03-30 | 徐波勇 | Method for synthesizing trifloxysulfuron |
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