GB1282493A - A process for the preparation of dithioesters - Google Patents

A process for the preparation of dithioesters

Info

Publication number
GB1282493A
GB1282493A GB5281569A GB5281569A GB1282493A GB 1282493 A GB1282493 A GB 1282493A GB 5281569 A GB5281569 A GB 5281569A GB 5281569 A GB5281569 A GB 5281569A GB 1282493 A GB1282493 A GB 1282493A
Authority
GB
United Kingdom
Prior art keywords
group
prepared
dithioesters
cooh
reaction
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
GB5281569A
Inventor
Nicholas Hay Leon
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.)
Unilever PLC
Original Assignee
Unilever PLC
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 Unilever PLC filed Critical Unilever PLC
Priority to GB5281569A priority Critical patent/GB1282493A/en
Priority to CA096,642A priority patent/CA944350A/en
Publication of GB1282493A publication Critical patent/GB1282493A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

1282493 Dithioesters UNILEVER Ltd 28 Oct 1969 52815/69 Heading C2C Dithioesters of the general formula are prepared by reacting a carboxyalkyl carbodithioate of the formula R. CS. SR<SP>2</SP> wherein R<SP>2</SP> is CH 2 COOH, (CH 2 ) 2 COOH, or CH(Me)CH 2 COOH and R is an organic radical, with a mercaptan of the formula R<SP>1</SP>SH wherein R<SP>1</SP> is an organic radical other than R<SP>2</SP>. The Specification refers to several novel dithioesters, which may be prepared by the above method, in which R is a phenyl group which may be substituted at the 2, 3 or 4 position with any one of an alkoxy, amido, halo, nitro, phenylazo or carbodithioate group, a homocyclic polynuclear aromatic group such as a naphthyl group, a heterocyclic group such as a furyl, 2-pyridyl, substituted 2-pyridyl group or the N-oxide group, or an alkyl group having from 1 to 24 carbon atoms, and in which R<SP>1</SP> is a phenyl group, benzyl group, alkyl or alkenyl group having from 1 to 6 carbon atoms or an alkylcarboxyalkyl group. The reaction is preferably carried out either in an organic solvent e.g. ether or benzene, and the thioglycollic acid by-product is removed by treatment of the reaction mixture with an aqueous alkaline solution e.g. NaOH, or in aqueous solution. The carboxyalkyl carbodithioates may be prepared either by reaction of a Grignard compound with carbon disulphide and subsequent esterification of the magnesium halide salt of the dithioacid with a chlorocarboxylic acid salt, or by thiohydrolysis of S-carboxyalkylthiopiperidinium bromide prepared by reacting a thiopiperide (prepared by the Willgerodt-Kindler method) and a bromocarboxylic acid.
GB5281569A 1969-10-28 1969-10-28 A process for the preparation of dithioesters Expired GB1282493A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB5281569A GB1282493A (en) 1969-10-28 1969-10-28 A process for the preparation of dithioesters
CA096,642A CA944350A (en) 1969-10-28 1970-10-27 Process for the preparation of dithioesters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5281569A GB1282493A (en) 1969-10-28 1969-10-28 A process for the preparation of dithioesters

Publications (1)

Publication Number Publication Date
GB1282493A true GB1282493A (en) 1972-07-19

Family

ID=10465419

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5281569A Expired GB1282493A (en) 1969-10-28 1969-10-28 A process for the preparation of dithioesters

Country Status (2)

Country Link
CA (1) CA944350A (en)
GB (1) GB1282493A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0128833A1 (en) * 1983-06-10 1984-12-19 Societe Nationale Elf Aquitaine (Production) Mono and dithio esters, their preparation and uses
US7662986B2 (en) * 1996-07-10 2010-02-16 Commonwealth Scientific And Industrial Research Organisation Polymerization with living characteristics

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0128833A1 (en) * 1983-06-10 1984-12-19 Societe Nationale Elf Aquitaine (Production) Mono and dithio esters, their preparation and uses
US4594150A (en) * 1983-06-10 1986-06-10 Societe Nationale Elf Aquitaine (Production) Mono- and dithioic esters, their preparation and uses
US7662986B2 (en) * 1996-07-10 2010-02-16 Commonwealth Scientific And Industrial Research Organisation Polymerization with living characteristics

Also Published As

Publication number Publication date
CA944350A (en) 1974-03-26

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees