GB809654A - 3:10-di-(4-carboxybutyl)-1:2:6:7-tetrathiacyclodiene and its salts and esters - Google Patents
3:10-di-(4-carboxybutyl)-1:2:6:7-tetrathiacyclodiene and its salts and estersInfo
- Publication number
- GB809654A GB809654A GB24472/55A GB2447255A GB809654A GB 809654 A GB809654 A GB 809654A GB 24472/55 A GB24472/55 A GB 24472/55A GB 2447255 A GB2447255 A GB 2447255A GB 809654 A GB809654 A GB 809654A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- bis
- dithio
- treating
- give
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D341/00—Heterocyclic compounds containing rings having three or more sulfur atoms as the only ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises the acid of the formula <FORM:0809654/IV (b)/1> and its salts and esters and their preparation by treating 6 : 61 - dithio - bis - (8 - thioloctanoic acid) or 8 : 81 - dithio - bis - (6 - thioloctanoic acid) or an alkyl ester thereof with a mild oxidizing agent such as a mixture of potassium iodide and iodine, preferably in an inert liquid reaction medium comprising a solvent such as methanol, ethanol, isopropanol, propanol, chloroform, ethyl acetate or butyl acetate. The esters may also be made by treating the acid with an equimolar quantity of a diazoalkane in ether. Salts are prepared by treating the acid with alkali metal or alkaline-earth metal carbonates, bicarbonates or hydroxides. The compounds are used as substitutes for a -lipoic acid. In an example, 6 : 61-dithio-bis - (8 - thioloctanoic acid) in chloroform, is treated with an aqueous solution of iodine and potassium iodide to give 3 : 10-di-(41-carboxybutyl) - 1 : 2 : 6 : 7 - tetrathiacyclo decane. Starting materials. 6 : 61 - Dithio - bis - (8-thioloctanoi acid) is made by treating 7-carbethoxy - 2 - heptenoic acid with thioacetic acid to obtain 3-acetylthio-7-carbethoxy heptanoic acid; reacting this with thionyl chloride to give 3-acetylthio-7-carbethoxy heptanoyl chloride; reducing with sodium borohydride to yield ethyl - 6 - acetylthio - 8 - hydroxyoctanoate; refluxing with sodium hydroxide in the presence of a trace of zinc dust to give 6 - thiol - 8 - hydroxyoctanoic acid; oxidizing with aqueous iodine-potassium iodide to give 6 : 61 - dithio - bis - (8 - hydroxyoctanoic acid) and condensing with thiourea to form a 6 : 61-dithio - bis }8 - [2(2 - thiopseudoureido)] - octanoic acid} which is hydrolysed to the desired bis-8-thiol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US809654XA | 1954-09-08 | 1954-09-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB809654A true GB809654A (en) | 1959-02-25 |
Family
ID=22160805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24472/55A Expired GB809654A (en) | 1954-09-08 | 1955-08-25 | 3:10-di-(4-carboxybutyl)-1:2:6:7-tetrathiacyclodiene and its salts and esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB809654A (en) |
-
1955
- 1955-08-25 GB GB24472/55A patent/GB809654A/en not_active Expired
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