GB688726A - Thiolurethanes and quaternary ammonium salts derived therefrom, and processes of producing same - Google Patents
Thiolurethanes and quaternary ammonium salts derived therefrom, and processes of producing sameInfo
- Publication number
- GB688726A GB688726A GB27780/50A GB2778050A GB688726A GB 688726 A GB688726 A GB 688726A GB 27780/50 A GB27780/50 A GB 27780/50A GB 2778050 A GB2778050 A GB 2778050A GB 688726 A GB688726 A GB 688726A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphate
- thiolurethanes
- reacting
- iodide
- quaternary
- Prior art date
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises thiolurethanes of the formula <FORM:0688726/IV (b)/1> wherein R1 and R2 are saturated hydrocarbon radicals, and their quaternary salts of the formula <FORM:0688726/IV (b)/2> wherein R1 and R2 are saturated hydrocarbon radicals, R is an alkyl radical and X is an anion. The thiolurethanes are prepared by reacting dimethylaminoethylthiol with a carbamyl chloride having two saturated hydrocarbon substituents, attached to the nitrogen atom, and may then be converted to the quaternary compounds by reacting them with an alkyl ester of an inorganic acid. The dimethylaminoethylthiol is prepared by reacting dimethylaminoethyl chloride with sodium hydrosulphide. Examples are given of the preparation of (1) dimethylaminoethylthiodibutylurethane; (2) the quaternary salt of (1) with ethyl iodide; (3) the sulphate prepared from (2) by the action of silver sulphate; (4) dimethylaminoethylthioldicyclohexylurethane; (5) the quaternary salt of (4) with ethyl iodide; (6) the sulphate corresponding to (5); (7), (9), (11) and (13) the quaternary salts of (4) with n-propyl iodide, n-butyl iodide, n-amyl iodide, and diethyl sulphate, respectively; (8), (10) and (12) the sulphates obtained by reacting (7), (9) and (11) with silver sulphate; (14) dimethylaminoethylthiodiamylurethane; (15) the quaternary salt of (14) with ethyl iodide; (16) the sulphate obtained from (15) by the action of silver sulphate; and (17) the quaternary salt of (14) with diethyl sulphate. The compounds have antispasmodic activity.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US688726XA | 1949-12-13 | 1949-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB688726A true GB688726A (en) | 1953-03-11 |
Family
ID=22085249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27780/50A Expired GB688726A (en) | 1949-12-13 | 1950-11-14 | Thiolurethanes and quaternary ammonium salts derived therefrom, and processes of producing same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB688726A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2913326A (en) * | 1956-01-25 | 1959-11-17 | Stauffer Chemical Co | Propyl-n, n-diethylthiolcarbamate and use as herbicide |
| US2913325A (en) * | 1956-01-25 | 1959-11-17 | Stauffer Chemical Co | Amyl-n, n-diethylthiolcarbamate and use as herbicide |
| US3228949A (en) * | 1958-09-18 | 1966-01-11 | Bayer Ag | Basic-substituted thioesters of carbamic acid |
-
1950
- 1950-11-14 GB GB27780/50A patent/GB688726A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2913326A (en) * | 1956-01-25 | 1959-11-17 | Stauffer Chemical Co | Propyl-n, n-diethylthiolcarbamate and use as herbicide |
| US2913325A (en) * | 1956-01-25 | 1959-11-17 | Stauffer Chemical Co | Amyl-n, n-diethylthiolcarbamate and use as herbicide |
| US3228949A (en) * | 1958-09-18 | 1966-01-11 | Bayer Ag | Basic-substituted thioesters of carbamic acid |
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