GB819199A - Novel -a-mercapto-amides and a process for the manufacture thereof - Google Patents

Novel -a-mercapto-amides and a process for the manufacture thereof

Info

Publication number
GB819199A
GB819199A GB3772/58A GB377258A GB819199A GB 819199 A GB819199 A GB 819199A GB 3772/58 A GB3772/58 A GB 3772/58A GB 377258 A GB377258 A GB 377258A GB 819199 A GB819199 A GB 819199A
Authority
GB
United Kingdom
Prior art keywords
acid
mercapto
acetic acid
dialkyl
diethyl
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
GB3772/58A
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 GB819199A publication Critical patent/GB819199A/en
Expired legal-status Critical Current

Links

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
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • 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
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises a -mercapto-amides of the formula <FORM:0819199/IV (b)/1> (wherein R represents an alkenyl or alkynyl group and R1 is a hydrogen atom or an alkyl or alkenyl group), and their preparation by (1) treating an a -halogen-a ,a -dialkyl-acetic acid with hydrogen sulphide, reacting the resulting a -mercapto-a ,a -dialkyl-acetic acid with a compound R-halogen, converting the a -(R-mercapto)-acetic acid so formed into its acid halide and reacting the latter with ammonia or an amine H2N-R1; or (2) converting an a -halogeno-a -a -dialkyl-acetic acid into its acid halide, treating the latter with ammonia or an amine H2N-R1 and reacting the acid amide so formed with a compound HS-R. Preferably, in method (1), the a -mercapto-a -a -dialkyl-acetic acid is condensed with the halide R-Halogen in a solvent (e.g. ethanol) in the presence of an acid binding agent (e.g. NaOMe) at ca. 20 DEG C.; the resulting a -(R-mercapto)-a ,a -dialkyl-acetic acid is converted into the corresponding acid halide in the usual manner, and the latter is reacted with an amine H2N-R1, advantageously in an inert solvent (e.g. ether). In examples, a -mercapto-a ,a -diethyl-acetic acid is alkenylated with allyl bromide and the resulting a - allylmercapto - a ,a - diethyl - acetic acid is converted, via the acid chloride, into a -alkylmercapto - a ,a - diethyl - acetamide and N-methyl - and N - allyl - a - allylmercapto - a ,a -diethyl-acetamide by reacting with ammonia, methylamine and allylamine respectively. Similarly, a - crotyl - and a - propargyl - mercapto-a ,a -diethylacetic acid and a -allyl-, a -crotyl- and a - propargyl - mercapto - isobutyric acid are prepared by alkenylating or alkynylating the appropriate a -mercapto acid, and converted into the corresponding acetamides and N-methylacetamides. In examples of method (2), a -bromo-a ,a -diethylacetic acid and a -bromoisobutyric acid are heated with thionyl chloride, the resulting acid chlorides are reacted with ammonia, and the amides are reacted with allyl mercaptan.ALSO:Therapeutic preparations, e.g. tablets, syrups or elixirs, for use as sedatives, muscle relaxants and tranquillizers, contain compounds of the general formula <FORM:0819199/VI/1> (wherein R represents an alkenyl or alkynyl group and R1 represents hydrogen or an alkyl or alkenyl group) in admixture with carriers and/or excipients.
GB3772/58A 1957-02-07 1958-02-05 Novel -a-mercapto-amides and a process for the manufacture thereof Expired GB819199A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US819199XA 1957-02-07 1957-02-07

Publications (1)

Publication Number Publication Date
GB819199A true GB819199A (en) 1959-09-02

Family

ID=22167238

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3772/58A Expired GB819199A (en) 1957-02-07 1958-02-05 Novel -a-mercapto-amides and a process for the manufacture thereof

Country Status (1)

Country Link
GB (1) GB819199A (en)

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