DE1768276C3 - Process for the preparation of ureidomethylphosphonium salts - Google Patents

Description

Rt Rl R ₄

"Y &

(I)

Have meaning with tertiary phosphines of the general formula

R ₄

PR ₄

R ₄

(IV)

in which the individual radicals R _{4 have} the aforementioned meaning, is reacted in the presence of an acid in at least an equivalent amount, based on starting material II.

in which the individual radicals R ₁ , R ₂ and R _{3 can be} identical or different and in each case an aliphatic, cycloaliphatic, araliphatic or aromatic radical, a hydrogen atom or the radical —CH ₂ OR ₅ , in which R _{5 is} a hydrogen atom or an aliphatic radical denotes, in addition, the radicals R ₂ and R ₃ can form a heterocyclic ring together with the adjacent ureido group, R ₁ , R ₂ and / or R ₃ also the radical

R ₄

»/
CH ₂ PR ₄

R ₄

30th

can mean, the individual radicals R _{4 can be} identical or different and each mean an aliphatic, cycloaliphatic, araliphatic or aromatic radical, X for an oxygen or sulfur atom, Y for the anion of an acid and η for 1, 2, 3 or 4 stands, characterized in that N-methylol or N-alkoxymethyl ureas of the general formula

X The subject of this invention is a process for the preparation of ureidomethylphosphonium salts of the general formula

R ₄

R ₁ -N '^ N-CH ₂ -PR ₄
R ₂ R ₃ R ₄

"Y (D

in which the individual radicals R ₁ , R ₂ and R _{3 can be} identical or different and in each case an aliphatic, cycloaliphatic, araliphatic or aromatic radical, a hydrogen atom or the radical —CH ₂ OR ₅ , in which R _{5 is} a hydrogen atom or an aliphatic radical denotes, in addition, the radicals R ₂ and R ₃ can form a heterocyclic ring together with the adjacent ureido group, R ₁ , R ₂ and / or R ₃ also the radical

N-CH ₂ OR ₅

I.
R ₈

(H)

45

in which the individual radicals R ₆ , R ₇ , R _{8 can be} identical or different and in each case an aliphatic, cycloaliphatic, araliphatic or aromatic radical, a hydrogen atom or the radical —CH ₂ OR ₅ , in which R _{5 is} a hydrogen atom or an aliphatic radical denotes, in addition, the radicals R ₇ and R ₈ together with the adjacent ureido group can form a heterocyclic ring, R ₅ and X have the aforementioned meaning, or instead of the starting materials II a mixture of formaldehyde and ureas of the general formula _v

* -N

NH

(111)

η of the radicals R ₆ , R ₇ and X the aforementioned -CH ₂ -PR ₄
R ₄

can mean, the individual radicals R _{4 can be} identical or different and each mean an aliphatic, cycloaliphatic, araliphatic or aromatic radical, X for an oxygen or sulfur atom, Y for the anion of an acid and η for 1, 2, 3 or 4 which is characterized in that N-methylol or N-alkoxymethyl ureas of the general formula II

R ₆ -N
R ₇

N-CH ₂ OR ₅

Rr

(Π)

in which the individual radicals R ₆ , R ₇ , R _{8 can be} identical or different and in each case an aliphatic, cycloaliphatic, araliphatic or aromatic Resl, a hydrogen atom or the radical —CH ₂ OR ₅ ,

before R ₅ denotes a hydrogen atom or an aliphatic test, denote, in addition, the radicals R _{7 and} R ₈ together with the adjacent ureido group: can form a heterocyclic ring, R ₅ and X have the aforementioned meaning, or instead of those starting materials II Mixture of formaldehyde and ureas of the general formula

Il c

R ₆ -N

NH

(ΠΙ)

in which the radicals R ₆ , R ₇ , R ₈ and X have the aforementioned meaning, with tertiary phosphines of the general formula

R ₄

(IV)

R ₄

in which the individual radicals R _{4 have} the aforementioned meaning, is reacted in the presence of an acid in at least an equivalent amount, based on starting material II.

The reaction can be carried out in the case of using Ν, Ν-dimethyl-N'-methylolurea, triphenylphosphine and hydrogen bromide represented by the following formulas:

CH ₃ C ₆ H ₅

NCONH-CH ₂ OH + PC ₆ H ₅ + HBr

C ₆ H ₅

CH ₃

C ₆ H ₅

40

CH ₃

NCONH-CH ₂ - PC ₆ H ₅
C ₆ H,

Br + H ₂ O can be substituted by alkyl groups with up to 6 carbon atoms and / or phenyl groups and X stands for an oxygen or sulfur atom.

It can e.g. B. the following N-methylol or N-alkoxymethyl ureas are used as starting material 11: N-methylol and Ν, Ν'-dimethylolethylene urea, N - methyl - N '- methylol - propylene urea, N, N' - di (methoxymethyl ) - 4 - oxotetrahydro-1,3,5 - oxadiazi n, N, N '- di - (methoxymethy 1) - ethylene urea, Ν, Ν, Ν'-trimethoxymethylurea, N ₁ N'-dimethylol - thiourea, N - Cyclohexyl - N '- methylolurea, N - benzyl - N' - methylol - urea, N - phenyl - N '- ethoxymethylurea, N - methoxymethyl - 2 - oxo - hexahydro - 1,3,5 - triazine.

Instead of the starting materials, mixtures of formaldehyde and ureas of the general formula IJI, which form starting material 11 during the reaction, can also be used. Preferred starting materials 111 are those in whose formula R ₆ , R ₇ , R ₈ and X have the aforementioned preferred meanings. In general, formaldehyde is used in such a mixture in a stoichiometric amount, based on the hydrogen atoms of starting material III which can be substituted on both nitrogen atoms. If there are several substituted hydrogen atoms on the nitrogen atoms and if only one hydrogen atom is to be substituted by formaldehyde, then only the amount of formaldehyde equivalent to this one hydrogen atom is used. Starting material III and formaldehyde can be fed to the reaction either separately or as a mixture. Formaldehyde can be added as an aqueous solution. But you can also formaldehyde-forming compounds under the reaction conditions, eg. B. paraformaldehyde, trioxane or methylene methyl ether, use. The reaction can be shown in the case of the use of N-methyl-propyleneurea as starting material III in the presence of hydrochloric acid by the following formulas:

45

The process according to the invention surprisingly provides a large number of ureidomethylphosphonium salts in good yield and purity and in a simple way.

N-methylol or N-alkoxy methylureas with 4.3 or preferably 1 or 2 methylol and / or alkoxymethyl groups of the general formula H attached to the nitrogen atoms are used as starting materials. Preferred starting materials 11 and correspondingly preferred end materials I are those in whose formulas the individual radicals R ₆ , R ₇ and R _{8 can be the} same or different and in each case an alkyl, cycloalkyl, aralkyl or aryl radical each having up to 10 carbon atoms, a hydrogen atom or the radical —CH ₂ OR ₅ and R ₅ denote a hydrogen atom or an alkyl radical with up to 6 carbon atoms, in addition the radicals R ₇ and R ₈ together with the adjacent ureido group also form a preferably 5- or 6-membered heterocyclic ring which In addition to the two nitrogen atoms of the ureido group, a further nitrogen atom can also contain an oxygen atom and also C ₆ H ₅

CH ₃ -N- ^ NH + CH ₂ O + PC ₆ H ₅ -t- HCl

C ₆ H,

CH

Ϊ
₃ —N ^A N-

C ₆ H ₅

-CH ₂ -PC ₆ H ₅
C _fi H,

CP + H ₂ O

It can e.g. B. the following ureas are used as starting materials III: urea, thiourea, N - methyl urea, N ₁ N '- dimethyl urea, N, N - dimethyl urea, N - ethyl - N' - propyl urea, ethylene urea, propylene urea, 5.5 - Dimethyl-propyleneurea, 4-methylpropyleneurea, 5,5-dimethyl-6-isopropyl-propyleneurea and the corresponding thioureas, 2-oxo-5-ethyl-hexahydro-1,3,5-triazine.

Tertiary phosphines of the general formula IV are obtained with the starting materials, usually in stoichiometric form Amount, based on the methylol and Alkoxymethy'igruppen of the starting material II, implemented. If the starting material 11 has several methylol and / or alkoxymethyl groups and you just want to

implement one or a part of these groups, see above. one uses only the number of to be converted Group-equivalent amount of phosphine IV. The reaction can also be carried out in various sub-steps perform by aian z. B. the starting material TII can only react with the equivalent amount of phosphine to be reacted, the Ureidomethylmonophosphoniunisalz thus formed is separated and in a further partial step with the appropriate Amounts of phosphine to the end product I converts. <o In an analogous manner, instead of the starting materials II also mixtures of formaldehyde and ureas III with corresponding amounts of phosphine 1V implemented. In the case of tetrahydro-oxadiazines or 2-oxo-hexahydrotriazines as starting "5 stoffeil and III are these with PhosphinenIV in stoichiometric amount, based on the methylol and alkoxymet ^ yl groups to be reacted Starting material II or UI implemented.

Preferred phosphines IV and correspondingly preferred end products 1 are those in whose formulas the individual radicals R _{4 can be} identical or different and each represent an alkyl, cycloalkyl, aralkyl or aryl radical with up to 10 carbon atoms. In the preferred end products I, R ₁ , R ₂ and R _{3 have} the aforementioned preferred meaning of R, “R ₇ and R ₈ , in addition, R ₁ , R ₂ and / or R _{3 can} each also be the radical

D.

t_ri ₂ r K ₄

R4

mean, and η stands for 1, 2, 3 or 4.

It can e.g. B. the following tertiary phosphines are used as starting materials IV: triphenylphosphine, Triethylphosphine, ethyl-diphenyl-phosphine, benzyl-phenyl-methylphosphine, tricyclohexyl-phosphine.

The reaction is carried out in the presence of an acid in at least an equivalent amount, based on the starting material 11 or the during the reaction from the mixture of formaldehyde and urea I II formed starting material II carried out. It is preferred to use 1 to 3 times the equivalent Amount of acid. Inorganic or organic acids can be used as the acid, e.g. B. hydrogen chloride, Sulfuric acid, phosphoric acid, hydrogen bromide, hydrogen iodide, hydrohalic acid, z. B. perchloric acid; aliphatic carboxylic acids, e.g. B. acetic acid; Sulfonic acids, e.g. B. p-toluenesulfonic acid, Benzenesulfonic acid; Polycarboxylic acids e.g. B. oxalic acid, adipic acid. The acid supplies the anion or the Anions that are necessary for the formation of the ureidomethyl mono- or polyphosphonium salts.

The reaction is carried out usually at a temperature between 0 and 100 ⁰ C, preferably between 40 and 8O ⁰ C, under atmospheric or superatmospheric pressure, continuously or discontinuously. It is expedient to use solvents which are inert under the reaction conditions, such as water; Alcohols e.g. B. methanol; cyclic ethers, e.g. B. dioxane or tetrahydrofuran; Ketones e.g. B. acetone or their mixtures.

The reaction can be carried out as follows: An N-Methvlol- or N-AlkoxvmethvlurstoffIl or the mixture of a urea III with formaldehyde are mixed together with a tertiary phosphine IV and at least an equivalent amount of acid and optionally the solvent with thorough mixing in a stirring apparatus reacted at the aforementioned temperature for ¹ I ₂ to 5 hours. The end product precipitates out of the reaction mixture on cooling and is filtered off or is separated off after the mixture has been evaporated and cooled. It is usually of sufficient purity and can, if necessary, be further purified by recrystallization.

The new compounds that can be made by the process of the invention are flame retardant finishes for textiles and valuable raw materials for the manufacture of textile finishing agents and pesticides. So can z. B. with them in an amount of 100 to 500 grams per liter of aqueous equipment liquor, if appropriate together with N-methylol compounds used in the anti-crease finish. Cotton fabric impregnated, dried and at temperatures between 80 to 160'C in a condensation unit treated and thus made flame-proof.

The parts given in the examples are parts by weight.

example 1
CH ₃ -N-CO-NH-CH ₃

C ₆ H ₅

CH ₃ -PC ₆ H

Br ¹

₆ "5

C ₆ H ₅

The mixture of 104.8 parts of triphynylphosphine in 1600 parts of methanol and 70 parts of 48% strength hydrogen bromide solution is treated with a mixture of 52.8 parts of Ν, Ν'-dimethyl-N-methoxymethylurea in 160 parts of methanol and heated to reflux temperature for 4 hours. After standing for one day the mixture at 0 C ^c, the precipitated end product is filtered off and dried. 118 parts of N ₁ N'-dimethyl ureido-N-methyltriphenylphosphonium bromide are obtained. This corresponds to a yield of 66.5% of theory. For purification, the product is recrystallized from methanol. M.p. 210 to 214 ° C. decomposition.

Analysis for C ₂₂ H ₂₄ ON ₂ PBr (443):

Calculated:

C 59.5, H 5.63, N 6.31, P 6.98, Br 18.00%;
found:

C 59.2, H 5.8, N 6.2, P 6.6, Br 17.8%.

Example 2
HIGH

(C ₆ H ₅ I ₃ P-CH ₂ -NCN-CH ₂ -P (C ₆ H ₅ ).,

2 cl

524 parts of triphenylphosphine are in 15,000 parts Dissolved methanol and with 2000 parts! Normal hydrochloric acid added in dioxane. For this solution one gives

148 parts of dimethylethylurea with thorough mixing. dissolved in 5 (X) parts of methanol, and allowed to stand at room temperature overnight. Concentration in a rotary evaporator gives a colorless residue, which when treated with Melhanol / liquid ester crystallized. 119 parts are obtained (70 "υ of the TIiC (H ie) lreido-N, N'-bis- [methyl-triphcnylphosphonium chloride] from melting point (from methanol / acetic acid) 200 C (with decomposition).

W ice ρ ic! 3

, Br,

Analysis for C _W H, “N ₂
Calculated:

C 60.7, H 4.68, N 3.64, P 8.05. Br 20.80%; found:

C 60.3, H 5.0. N 3.8, P 7.4, Br 21.1%.

Example 4

(C ₁₁ U ₅ )., P CH, -NC N-CH ₂

P (C ₆ H ₅ )., - CH ₂ -NC- N-CH ₂ - P (C ₆ H ₅ ),

2 Br "

2 Br '5

52.4 parts triphynylphosphine are used in 1200 parts Dissolved methanol and treated with 50 parts of 48 percent strength by weight hydrobromic acid. To this 14.8 parts of diniethoxymethylurea are added to the solution and let the mixture stand for 30 minutes at room temperature. When concentrating on a rotary evaporator with the simultaneous injection of ethyl acetate, the end product is immediately obtained in the form of a colorless one Crystals. 70 parts (90% of theory) of ureido - N.N - bis [methyl - triphenyl - phosphonium bromide] are obtained, Kp. (From melhanol / vinegar ester or acetonitrile! about 250 C (with decomposition!

52.4 parts of triphenylphosphine are dissolved in 1200 parts of methanol and 50 parts of 48% bromine hydrochloric acid added. To this end, 16.4 parts of dimethoxymethyl thiourea are added with stirring 800 parts of methanol. After an hour there will be; Solvent stripped off on a rotary evaporator and the residue crystallized from methanol / ethyl acetate. 49.5 parts are obtained (62% of theory Thioureido - N, N '- bis - [methyl - triphenylphosphonium bromide], m.p. 232 "C (with decomposition).

Analysis for C ₃₉ H ₃₆ S ₁ P ₂ N ₂ Br ₂ :
Calculated:

C 59.5. H 4.58. S 4.07, P 7.89. N 3.56. Br 20.35% found:

C 59.1. H 4.9, S 3.8. P 7.0. N 3.4. Br 20.4%.

Example PlC ₁₁ H ₅ ), CH, N --- C - N-CH ₂ - P (C ₁₁ H ₅ I ₃

! i 1

H O H 2J

2H ₂ O

1 np

pheni! phosphine are in 5 (H) IcUCn Dissolved methanol and treated with 33 parts of 57% strength hydriodic acid. For this one gives under Stir a solution of 7.4 parts of dimethoxymethylurea in 100 parts of methanol and stir for about 10 minutes. The solvent is on The rotary evaporator was concentrated and ethyl acetate was added. 22 parts are obtained (51% of theory) Ureido - N.N '- bis - [methyl - triphenylphosphonium iodide], Mp. (From methanol) 230 ° C. (with decomposition).

Analysis for C ₁₁ H ^ N ₂ PJ,:
Calculated:

C 55.18. H 4.12. N 3.21, P 7.09. J 29.10%;
found:

C 54.5. H 4.3. N 3.Z P 6.9. J 28.9%.

1 hour after. The solvent is stripped off on a rotary evaporator and the residue with ethyl acetate offset. 65 parts (80% of theory) are obtained. Ureido - N.N '- bis - [methyl - triphenylphosphonium perchlorate], Mp. (From methanol) 229 ° C. (with decomposition).

Analysis for C ₃₉ H ₃₆ N ₂ CL ₂ P ₂ :

Calculated:

C 58.90. H 4.45. N 3.47. Cl 8.78. P 7.67%: found:
~ C 58.2. H 4.8. N 3.7. Cl 8.6. P 7.6%.

Example 7 Example 6

! O

P (C ₆ H ₅ I ₃ -CH ₂ - NC N-CH ₂ -HH

55

Γ /

C ₆ H ₅ -P-CH ₂ -HNCON 2ClOf 60 ^ h. \

C ₆ H ₅

C ₆ H ₅

52.4 parts of triphenylphosphine are dissolved in 1,500 parts of methanol, and 180 parts of a 20% strength aqueous perchloric acid are added. 14.8 parts of dimethoxymethyl · larnstoff, dissolved in 50 parts of methanol, are added to this solution while stirring, and CH ₂ —PC is stirred ₆ H ₅

C ₆ H ₅

In a stirred apparatus, 39.3 parts of triphenylphosphine are dissolved in 800 parts of methanol and mixed with 25.3 parts of 48% strength hydrogen bromide solution are added 9.6 parts are added to this solution with stirring

609629/70

Ν, Ν, Ν'-trimethoxymethylharnslofr added. The The reaction mixture is heated at 50 ° C. for 3 hours. After cooling, the precipitated end product is vacuumed and dried. 43 parts of ureido

10

(ns- Ν.Ν, Ν '- {methyl-triphenylphosphonium bromide! echo. This corresponds to a yield of 77.4% of theory. The product can be used for cleaning Methanol are recrystallized. Mp 202-205 "C.

example

C ₁₁ H ₅

C "H, -P-CH, -N N-CII ₁ -P -QH ₅ 2 Br

'I "I I' I

C "H ₅ CH ₂ CH, Q ₁ H ₅

\ / CH,

In a stirring apparatus, 104.8 parts of triphynylphosphine are dissolved in 8 (X) parts of methanol and 100 parts of 48% hydrogen bromide solution, a solution of 37.6 parts of Ν, Ν'-dimethoxyinelhylpropylenehainstoff given in 80 parts of methanol. The reaction mixture is heated to 64 to 65 ° C. for 3 hours held and then cooled to OX.

After standing for one day, the end product is filtered off and dried. 149 parts of propylene urea-N, N'-di - (methyl-triphenylphosphonium bromide) are obtained. This corresponds to a yield of 92% of theory. For purification, the product can be recrystallized from methanol. Mp. 240 ° C. (with decomposition).

Analysis Rir C ₄₂ H ₄₁₁ ON ₂ P ₂ Br, (810): Calculated:

C 62.2. H 4.94, N 3.46. P 7.65. Ur 19.76%; found:

C 62.0. H 4.9. N 3.30. P 7.00. Br 19.00%.

example

(CJIO ₁ P-CH ₁ -NC- N-CH, - P (CJI ₅ ),

* I I

CH, CH,

2CT

52.4 parts Triphcnylphosphin are in 1500 parts Dissolve methanol and add 200 parts of normal hydrochloric acid added in dioxane. To this cold solution of the phosphonium salt is added while swirling 14.6 parts of diethylolethylene urea. solved in 100 parts of methanol. The mixture is left to stand overnight and is concentrated thinly at 30 to 40 ° C. in a rotary evaporator to dry up. A colorless resin remains, which when treated with dimethylformamide Ethyl acetate crystallizes. 64 parts (90% of theory) of 2-oxo-imidazolidinyl-N, N'-bis [methyl-phenylphosphonium chloride] are obtained. Mp. (From methanol / ethyl acetate) about 230 ° C. (with decomposition).

example

CH ₂ - N-CH ₂ -PC ₆ H ₅ 2 Br

CH,

QH ₅

In 800 parts of methanol, 52.4 parts of triphenylphosphine are added with 36 parts of 48% strength Dissolved hydrogen bromide solution. A mixture of 19 parts of Ν, Ν'-dimethoxymethylfithylenethiourea in 200 parts of methanol is added to this solution. The reaction mixture is heated to reflux temperature (66 ° C.) for 3 hours and then cooled to ^{0 ° C.} After standing for one day, the precipitated end product is filtered off with suction and dried. There are 52 parts of ethylene thiourea-N, N'-di- (methyltri- phenylphosphonium bromide) obtained; this corresponds to a yield of 64% of theory. For cleaning the product can be recrystallized from methanol. Mp. 228 to 235 ° C (with decomposition).

Analysis for C ₄₁ H ₃₈ N ₂ P ₂ Br ₂ S (812): Calculated:

C 60.6, H 4.68, N 3.45, P 7.63, Br 19.7, S 3.94%; found:

C 60.2, H 4.7, N 3.3, P 7.4, Br 19.3, S 4.1%.

example O

Q ₁ H ₅ -P-CH ₂ -N N-CH ₂ -PQ ₁ H ₅ 2 Br °

Q ₁ H ₅ CH ₂ CH ₂ Q ₁ H ₅

For mixing 52.4 parts of triphenylphosphine in 800 parts of methanol and 30 parts of 48% strength hydrogen bromide solution 19 parts of N, N'-dimethoxymethyl-4-oxo-telrahydro-1,3,5-oxadiazine with stirring added. After three hours of heating at 50 ° C., the mixture is cooled to room temperature and after the precipitated end product is filtered off after standing for one day. There are 63 parts of 4-oxo-tetrahydro-1,3,5-oxadiazinyl - N.N '- di - (methyl - triphenyl - phosphonium bromide) obtained. This corresponds to a yield of 77.5% of theory. For purification, the product is recrystallized from methanol. Mp 221-223 ° C (with decomposition).

Analysis C ₄₁ H ₃₈ O ₂ N ₂ P ₂ Br ₂ (812): Calculated:

C 60.6, H 4.78, N 3.45, P 7.64, Br 19.7%; found:

C 59.8, H 5.00, N 3.20, P 7.30. Br 19.0%.

tionwcise added. The mixture remains above Nachi, then the methanol is stripped off on a rotary evaporator. A yellow resin remains, which is taken up in methanol and precipitated in crystalline form by adding ethyl acetate. 29 parts (41% of theory) of 2-oxo-N-methoxymethylhexahydropyrimidyl-N'-methyl-triphenylphosphonium bromide are obtained. Mp. (From methanol / Essigester) 210 ⁰ C (untei decomposition).

Example 13
O

CH ₁ -OCH ₂ -N

N-CH ₂ -P (C ₆ Hj) ₃

Example 12 O

CH ₁ C) -CH ₂ -N

CH,

N-CH ₂ -P (C ₆ Hs) ₃

CH ₂

CH ₂

Br 34.8 parts of Ν, Ν'-dimethoxy-methyl-ethylene urea are dissolved in 1600 parts of methanol and hierzi a solution of 52.4 parts of triphenylphosphine and 50 parts of 48% hydrobromic acid within 3 hours slowly added in 1200 parts of methanol. The mixture stays overnight, then the solvent is drawn off on a rotary evaporator while simultaneously injecting ethyl acetate. 48.5 parts are obtained (50% of theory of 2-oxo-imidazolidinyl-N-methoxylmethyl-N'-me ethyl triphenyl phosphonium bromide. Mp. (From methanol / ethyl acetate) 175 ° C. (with decomposition).

37.6Parts of Ν, Ν'-dimethoxymethyl propylene urine 45 analysis for C ₂₄ H ₂₆ O ₂ N ₂ P Br:

substance are dissolved in 1600 parts of methanol and within of 3 hours with stirring a solution of 52.4 parts of triphenylphosphine and 50 parts of 48% strength Hydrobromic acid in 1200 parts of methanol por-

Calculated:

C 59.4, H 5.36, O 6.47, N 5.65, P 6.27, Br 16.4% found:

C 59.4, H 5.4, O 4.7, N 6.1, P 6.5, Br 17.4%.

CH, -N N — CH, -

77.0 parts of phenylbenzylmethylphosphine are mixed with 360 parts of normal methanolic hydrochloric acid in a Schlenk tube under nitrogen. Then 31.3 parts of dimethoxymethylethyleneurea are added with stirring. dissolved in 200 parts of methanol, added, and the mixture is stirred for 1 hour at room temperature. The solvent is on the Ro- 2 CP

tation evaporator removed and the Rückstanc mixed with ethyl acetate. A yellowish resin is obtained that crystallizes after a few days. 80.2 parts (74% of theory) of 2-oxo-imidazolidinyl are obtained N, N '- bis - [methyl - (phenyl - benzyl - methyl - phosphonium chloride)] with a melting point of 125 ° C (from methanol, Ethyl acetate, with decomposition).

Claims (1)

Claim: Process for the preparation of ureidomethylphosphonium salts of the general formula ! I CR ₄ R ₁ -N N-CH ₂ -PR ₄