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US4401604A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparing thiosulfenamide derivatives of N-phosphonomethylglycine triesters

Assignee: Monsanto Co
•
Filing: 1981-10-05
•
Granted: 1983-08-30
•
Expires: 2001-10-05
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Abstract

Abstract This invention relates to a process for preparing sulfenyl chloride derivatives of N-phosphonomethylglycine triesters which are useful as herbicides or intermediates for the production of thiosulfenamide derivatives of N-phosphonomethylglycine triesters compounds which are useful as herbicides.

Inventors

  • 👤 James A. Sikorski
  • 👤 Mary A. Hoobler

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 23:46
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/40; C07F9/4003; C07F9/4006; A; A01; A01N; A01N57/00; A01N57/18; A01N57/22

Claims Analysis

Total Claims: 38
Claim 1
Independent Claim 181 words
A process for preparing a compound of the formula ##STR5## wherein R is selected from the group consisting of phenyl, naphthyl, biphenylyl; or phenyl, naphthyl or biphenylyl substituted with from 1 to 3 substituents, independently selected from the group consisting of lower alkyl, lower alkoxy, lower alkylthio, lower alkoxycarbonyl, methylenedioxy, trifluoromethyl, cyano, nitro and halogen; and R 1 is independently alkyl, cycloalkyl, aralower alkyl, phenyl, naphthyl or phenyl or naphthyl substituted with from 1 to 3 substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halogen, trifluoromethyl and nitro, and R 2 is lower alkyl or aralower alkyl which comprises reacting a compound of the formula ##STR6## wherein R and R 2 are as aforedefined with SCl 2 aprotic solvent and in the presence of a hydrogen chloride acceptor to form a compound of the formula ##STR7## wherein R and R 2 are as above defined, and reacting said compound of formula (III) with a compound of the formula R.sub.1 SH (IV) to form said compound of formula (I) and in the presence of a hydrogen chloride acceptor.
Claim 2
Dependent Claim 181 words
A process for preparing a compound of the formula ##STR5## wherein R is selected from the group consisting of phenyl, naphthyl, biphenylyl; or phenyl, naphthyl or biphenylyl substituted with from 1 to 3 substituents, independently selected from the group consisting of lower alkyl, lower alkoxy, lower alkylthio, lower alkoxycarbonyl, methylenedioxy, trifluoromethyl, cyano, nitro and halogen; and R 1 is independently alkyl, cycloalkyl, aralower alkyl, phenyl, naphthyl or phenyl or naphthyl substituted with from 1 to 3 substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halogen, trifluoromethyl and nitro, and R 2 is lower alkyl or aralower alkyl which comprises reacting a compound of the formula ##STR6## wherein R and R 2 are as aforedefined with SCl 2 aprotic solvent and in the presence of a hydrogen chloride acceptor to form a compound of the formula ##STR7## wherein R and R 2 are as above defined, and reacting said compound of formula (III) with a compound of the formula R.sub.1 SH (IV) to form said compound of formula (I) and in the presence of a hydrogen chloride acceptor.
Claim 3
Dependent Claim 9 words
The process of claim 1, wherein R is phenyl.
Claim 4
Dependent Claim 10 words
The process of claim 2, wherein R 1 is alkyl.
Claim 5
Dependent Claim 10 words
The process of claim 3, wherein R 1 is methyl.
Claim 6
Dependent Claim 10 words
The process of claim 2, wherein R 1 is cycloalkyl.
Claim 7
Dependent Claim 10 words
The process of claim 5, wherein R 1 is cyclohexyl.
Claim 8
Dependent Claim 10 words
The process of claim 2, wherein R 1 is araloweralkyl.
Claim 9
Dependent Claim 10 words
The process of claim 7, wherein R 1 is phenylethyl.
Claim 10
Dependent Claim 10 words
The process of claim 3, wherein R 1 is isopropyl.
Claim 11
Dependent Claim 10 words
The process of claim 3, wherein R 1 is n-octyl.
Claim 12
Dependent Claim 11 words
The process of claim 3, wherein R 1 is tertiary alkyl.
Claim 13
Dependent Claim 11 words
The process of claim 11, wherein R 1 is tertiary butyl.
Claim 14
Dependent Claim 10 words
The process of claim 3, wherein R 2 is alkyl.
Claim 15
Dependent Claim 10 words
The process of claim 13, wherein R 2 is methyl.
Claim 16
Dependent Claim 11 words
The process of claim 3, wherein R 2 is aralower alkyl.
Claim 17
Dependent Claim 10 words
The process of claim 15, wherein R 2 is phenylmethyl.
Claim 18
Dependent Claim 34 words
The process of claim 2, wherein R 1 is phenyl or phenyl substituted with from 1 to 3 substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halogen, trifluoromethyl and nitro.
Claim 19
Dependent Claim 19 words
The process of claim 1 wherein R is 4-chloro-3-methyl, phenyl R 2 is ethyl and R 1 is 4-methoxyphenyl.
Claim 20
Dependent Claim 18 words
The process of claim 2 wherein R is phenyl, R 2 is methyl and R 1 is 1,1-dimethylethyl.
Claim 21
Dependent Claim 18 words
The process of claim 2 wherein R is 4-methoxyphenyl, R 2 is ethyl and R 1 is 1,1-dimethylethyl.
Claim 22
Dependent Claim 18 words
The process of claim 2 wherein R is phenyl, R 2 is phenylmethyl and R 1 is 1,1-dimethylethyl.
Claim 23
Dependent Claim 18 words
The process of claim 2 wherein R is phenyl, R 2 is methyl and R 1 is 4-methylphenyl.
Claim 24
Dependent Claim 18 words
The process of claim 2 wherein R is 4-methoxyphenyl, R 2 is phenylmethyl and R 1 is naphthyl.
Claim 25
Dependent Claim 18 words
The process of claim 2 wherein R is 4-methoxyphenyl, R 2 is phenylmethyl and R 1 is 4-chlorophenyl.
Claim 26
Dependent Claim 9 words
The process of claim 2 wherein R is 4-chloro-3-methylphenyl.
Claim 27
Dependent Claim 15 words
The process of claim 2, wherein R 1 is isopropyl and R 2 is methyl.
Claim 28
Dependent Claim 10 words
The process of claim 2 wherein R 2 is ethyl.
Claim 29
Dependent Claim 10 words
The process of claim 2 wherein R 1 is 4-methoxyphenyl.
Claim 30
Dependent Claim 25 words
The process of claim 2, wherein said aprotic solvent comprises benzene, toluene, dichloromethane, tetrahydrofuran, dichloromethane, cyclohexane, methylcyclohexane, hexane, octane, dioxane, ethyl ether and mixtures thereof.
Claim 31
Dependent Claim 11 words
The process of claim 29, wherein said aprotic solvent comprises toluene.
Claim 32
Dependent Claim 13 words
The process of claim 30, wherein said hydrogen chloride acceptor is an amine.
Claim 33
Dependent Claim 12 words
The process of claim 31, wherein said amine is a tertiary amine.
Claim 34
Dependent Claim 11 words
The process of claim 32, wherein said tertiary amine is triethylamine.
Claim 35
Dependent Claim 23 words
The process of claim 33, wherein the temperature of said reaction is in the range from about -50° C. to about 100° C.
Claim 36
Dependent Claim 20 words
The process of claim 34, wherein said temperature is in the range from about -30° C. to about +10° C.
Claim 37
Dependent Claim 27 words
The process of claim 1, wherein the reaction of said compound of formula (II) with sulfur dichloride is carried out in the presence of an aprotic solvent.
Claim 38
Dependent Claim 30 words
The process of claim 1, wherein the reaction of said compound of formula (III) with said compound of formula (IV) is carried out in the presence of our aprotic solvent.

References Cited (Backward Citations)

US2123082A Cited
US3155720A Cited
US4120689A Cited
US4201733A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-08-29 1987-02-28 1987-08-30 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-08-29 1991-02-28 1991-08-30 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-08-29 1995-02-28 1995-08-30 $7700.00 Window Closed / Lapsed

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