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 esters

Info

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
Application number
GB210/44A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB574279A publication Critical patent/GB574279A/en
Expired legal-status Critical Current

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.
GB210/44A 1943-02-17 1944-01-05 Process for the manufacture of derivatives of thiophane-3-one-4-carboxylic acid esters Expired GB574279A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (4)

* Cited by examiner, † Cited by third party
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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