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Process for the preparation of acylaminomethanephosphonic acids
| Details |
Inventors: Kleiner, Hans-Jerg;
Assignee: Hoechst Aktiengesellschaft (Frankfurt am Main, DE)
Primary Examiner: Dees; Jose G.
Assistant Examiner: Frazier; B.
Attorney, Agent or Firm: Curtis, Morris & Safford
Acylaminomethanephosphonic acids are useful intermediates for the preparation of the herbicide N-phosphonemethylglycine and its salts. According to the invention, acylaminomethanephosphonic acids of the formula (I) R.sup.1 --CO--NHCH.sub.2 P(.dbd.O) (OH).sub.2 (I) in which R.sup.1 is H, C.sub.1 -C.sub.6 -alkyl, benzyl or optionally substituted phenyl, can be prepared in a process which can be employed industrially, which comprises the reaction of the compound of the formula R.sup.1 --CO-NH--CH.sub.2 OH with P.sub.2 O.sub.3 and then hydrolysis with water. |
|
DETAILED DESCRIPTION I claim: 1.
A process for the preparation of a compound of the formula I ##STR2## in which R.
sup.
1 is H, C.
sub.
1 -C.
sub.
6 -alkyl, benzyl or phenyl, which is unsubstituted or substituted by one or more radicals from the group comprising C.
sub.
1 -C.
sub.
4 -alkyl, C.
sub.
1 -C.
sub.
4 -alkoxy and halogen, which comprises reacting a compound of the formula II R.
sup.
1 --CO--NH--CH.
sub.
2 --OH (II) in which R.
sup.
1 has the abovementioned meaning, with diphosphorus trioxide (P.
sub.
2 O.
sub.
3) and then hydrolyzing with water.
2.
The process as claimed in claim 1, wherein R.
sup.
1 is H, C.
sub.
1 -C.
sub.
3 -alkyl, benzyl or phenyl.
3.
The process as claimed in claim 1, wherein R.
sup.
1 is hydrogen, methyl, ethyl or phenyl.
4.
The process as claimed in claim 1, wherein R.
sup.
1 is methyl.
5.
The process as claimed in claim 1, wherein R.
sup.
1 is phenyl.
6.
The process as claimed in claim 1, wherein the compound of the formula II and P.
sub.
2 O.
sub.
3 are reacted in a molar ratio II:P.
sub.
2 O.
sub.
3 of at most 2:1.
7.
The process as claimed in claim 6, wherein the molar ratio is from 2:1 to 1.
5:1.
8.
The process as claimed in claim 1, wherein the reaction temperature for the reaction with P.
sub.
2 O.
sub.
3 is 60.
degree.
to 200.
degree.
C.
9.
The process as claimed in claim 1, wherein the hydrolysis is carried out with water in a molar ratio of water to P.
sub.
2 O.
sub.
3 employed of at least 1:1 and at a temperature of 10.
degree.
to 200.
degree.
C.
10.
The process as claimed in claim 1, wherein the reaction of the compound of the formula II and P.
sub.
2 O.
sub.
3 is carried out in the presence of an organic solvent.
11.
The process as claimed in claim 10, wherein the solvent is an inert polar protic or aprotic organic solvent.
12.
The process as claimed in claim 6, wherein R.
sup.
1 is H, C.
sub.
1 -C.
sub.
3 -alkyl, benzyl or phenyl.
13.
The process as claimed in claim 12, wherein the molar ratio is from 2:1 to 1.
5:1.
14.
The process as claimed in claim 12, wherein the reaction temperature for the reaction with P
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