GB574279A - Process for the manufacture of derivatives of thiophane-3-one-4-carboxylic acid esters - Google Patents
Process for the manufacture of derivatives of thiophane-3-one-4-carboxylic acid estersInfo
- Publication number
- GB574279A GB574279A GB210/44A GB21044A GB574279A GB 574279 A GB574279 A GB 574279A GB 210/44 A GB210/44 A GB 210/44A GB 21044 A GB21044 A GB 21044A GB 574279 A GB574279 A GB 574279A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl ester
- acid
- sulphide
- propionic acid
- ester
- 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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Derivatives of thiophane-3-one-4-carboxylic acid esters of formula <FORM:0574279/IV/1> where R represents a lower alkyl group and X an aliphatic radical, are prepared by treating b -propionic acid -(X-acetic acid)-ester sulphides with an alkaline condensing agent. Suitable condensing agents mentioned include lower alkali alcoholates, and alkali amides. Radicals which are represented by X include -CH2.CH2.COOC2H5, -CH2.CH2.CH2.OCH3, -(CH2)4.OCH3, and -(CH2)4CN. In examples: (1) b -propionic acid-(a -glutaric acid)-ester sulphide is added to a toluene solution of sodium ethylate to form 2-(carbethoxy-ethyl)-thiophane-3-one-4-carboxylic acid ethyl ester. (2) b -propionic acid-a -(o -methoxy capronic acid) ethyl ester sulphide is ring-closed as in example (1). b -Propionic acid-(a -glutaric acid)-ester sulphide is made by adding b -mercapto-propionic acid ethyl ester to a solution of sodium in alcohol followed by a -bromo glutaric acid ester, and refluxing the reactants. b -Propionic acid a -(o -methoxy capronic acid) ethyl ester sulphide is made by adding a -bromo-o -methoxy capronic acid ethyl ester to a sodium ethylate solution of b -mercapto propionic acid ethyl ester. Samples have been filed under Section 2 (5) of: (1) 2-(o -methoxy-propyl)-thiophane-3-one-4-carboxylic acid ethyl ester made by adding b -mercapto-propionic acid ethyl ester and a -bromo-o -methoxy-valeric acid ethyl ester to a solution of sodium in alcohol, and treating the b -propionic acid-g -(o -methoxy valeric acid ethyl ester) ethyl ester sulphide with sodium ethylate under reflux. (2) 2-(o -carbethoxybutyl) - thiophanone - (3) - carboxylic acid - (4) - ethyl ester made by adding a toluene solution of (b -carbethoxy-ethyl) - (a 1, e 1-di-carbethoxy-amyl) sulphide to a suspension of sodium in a toluene-alcohol solvent, and heating under reflux. (3) 2-(o -cyanobutyl)-thiophanone-(3)-carboxylic acid-(4)-ethyl ester made by heating in sodium ethylate solution (b - carbethoxy - ethyl) - (a 1 - carbomethoxy - o 1 - cyano - n - amyl) - sulphide.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH574279X | 1943-02-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB574279A true GB574279A (en) | 1945-12-31 |
Family
ID=4521101
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB210/44A Expired GB574279A (en) | 1943-02-17 | 1944-01-05 | Process for the manufacture of derivatives of thiophane-3-one-4-carboxylic acid esters |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB574279A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4299968A (en) | 1973-12-03 | 1981-11-10 | Hoffmann-La Roche Inc. | Novel thiophene compounds |
US4317915A (en) | 1976-08-23 | 1982-03-02 | Hoffmann-La Roche Inc. | Novel thiophene derivatives |
US4360681A (en) | 1973-12-03 | 1982-11-23 | Hoffmann-La Roche Inc. | Novel thiophene compounds |
US4428963A (en) | 1976-08-23 | 1984-01-31 | Hoffmann-La Roche Inc. | Novel thiophene derivatives |
-
1944
- 1944-01-05 GB GB210/44A patent/GB574279A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4299968A (en) | 1973-12-03 | 1981-11-10 | Hoffmann-La Roche Inc. | Novel thiophene compounds |
US4360681A (en) | 1973-12-03 | 1982-11-23 | Hoffmann-La Roche Inc. | Novel thiophene compounds |
US4317915A (en) | 1976-08-23 | 1982-03-02 | Hoffmann-La Roche Inc. | Novel thiophene derivatives |
US4428963A (en) | 1976-08-23 | 1984-01-31 | Hoffmann-La Roche Inc. | Novel thiophene derivatives |
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