US4401604A
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Process for preparing thiosulfenamide derivatives of N-phosphonomethylglycine triesters
Assignee: Monsanto Co
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Filing: 1981-10-05
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Granted: 1983-08-30
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Expires: 2001-10-05
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)
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 |