GB820954A - Improvements in or relating to esters of 2,3-dimercaptopropanol - Google Patents
Improvements in or relating to esters of 2,3-dimercaptopropanolInfo
- Publication number
- GB820954A GB820954A GB1356956A GB1356956A GB820954A GB 820954 A GB820954 A GB 820954A GB 1356956 A GB1356956 A GB 1356956A GB 1356956 A GB1356956 A GB 1356956A GB 820954 A GB820954 A GB 820954A
- Authority
- GB
- United Kingdom
- Prior art keywords
- esters
- substituted
- acetate
- alcohol
- benzoate
- 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
- 150000002148 esters Chemical class 0.000 title abstract 4
- WQABCVAJNWAXTE-UHFFFAOYSA-N dimercaprol Chemical compound OCC(S)CS WQABCVAJNWAXTE-UHFFFAOYSA-N 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- -1 carboxylic acid halide Chemical class 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- IKCLCGXPQILATA-UHFFFAOYSA-M 2-chlorobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-M 0.000 abstract 1
- YYKVTJNAMNQKIU-UHFFFAOYSA-N 3,3-bis(sulfanyl)propan-1-ol Chemical compound OCCC(S)S YYKVTJNAMNQKIU-UHFFFAOYSA-N 0.000 abstract 1
- SHLSSLVZXJBVHE-UHFFFAOYSA-N 3-sulfanylpropan-1-ol Chemical compound OCCCS SHLSSLVZXJBVHE-UHFFFAOYSA-N 0.000 abstract 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-M 4-chlorobenzoate Chemical compound [O-]C(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-M 0.000 abstract 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- APTGPWJUOYMUCE-UHFFFAOYSA-N S-Ethyl thioacetate Chemical compound CCSC(C)=O APTGPWJUOYMUCE-UHFFFAOYSA-N 0.000 abstract 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000002365 anti-tubercular Effects 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000007717 exclusion Effects 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229940049953 phenylacetate Drugs 0.000 abstract 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
O-esters of 2:3-dimercapto propanol are prepared by a process wherein the alcohol is reacted by contacting, if necessary with heating, with a carboxylic acid halide of the general formula R.COX, wherein R is a substituted alkyl group or a substituted or unsubstituted aryl, aralkyl or cycloalkyl group, the substituents being such as are inert under the conditions of the reaction, and X is a halogen atom. The reaction is preferably effected with acid chlorides and in the presence of a liquid which is a solvent for the alcohol and the acid halide, especially a hydrocarbon solvent. Examples describe the preparation of the following O-esters of 2:3-mercapto propanol by refluxing the alcohol with the appropriate acid chloride in benzene with exclusion of moisture: (1) benzoate, (2) phenyl acetate, (3) o-chlorobenzoate, (4) p-chlorobenzoate, (5) p-methoxy benzoate, (6) hexahydrobenzoate, (7) b -methyl thiopropionate, (8) ethylthio acetate, (9) benzyl thio acetate, (10) 2:4-dichlorobenzoate, (11) a -naphthoate and (12) p-(p-toluene sulphonamido) benzoate. Certain of these esters have anti-tubercular activity. According to the Provisional Specification, the esters may be prepared from acid halides of the general formula R1COX, wherein R1 is a substituted, e.g. halo-substituted, or unsubstituted alkyl, aryl, aralkyl or cyclo-alkyl group and an additional example is given employing palmityl chloride as reagent. The esters, with the exception of the acetate, propionate, butyrate and the succinate, are stated to be new compounds. Specification 687,069 is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1356956A GB820954A (en) | 1956-05-02 | 1956-05-02 | Improvements in or relating to esters of 2,3-dimercaptopropanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1356956A GB820954A (en) | 1956-05-02 | 1956-05-02 | Improvements in or relating to esters of 2,3-dimercaptopropanol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB820954A true GB820954A (en) | 1959-09-30 |
Family
ID=10025337
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1356956A Expired GB820954A (en) | 1956-05-02 | 1956-05-02 | Improvements in or relating to esters of 2,3-dimercaptopropanol |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB820954A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013503908A (en) * | 2009-09-04 | 2013-02-04 | ユナイテッド パラゴン アソシエイツ インコーポレイテッド | Compounds for treating disorders or diseases associated with neurokinin 2 receptor activity |
-
1956
- 1956-05-02 GB GB1356956A patent/GB820954A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013503908A (en) * | 2009-09-04 | 2013-02-04 | ユナイテッド パラゴン アソシエイツ インコーポレイテッド | Compounds for treating disorders or diseases associated with neurokinin 2 receptor activity |
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