GB1014911A - Process for the production of isonitriles - Google Patents

Process for the production of isonitriles

Info

Publication number
GB1014911A
GB1014911A GB834163A GB834163A GB1014911A GB 1014911 A GB1014911 A GB 1014911A GB 834163 A GB834163 A GB 834163A GB 834163 A GB834163 A GB 834163A GB 1014911 A GB1014911 A GB 1014911A
Authority
GB
United Kingdom
Prior art keywords
glycine
halides
thioformyl
isocyano
chloride
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
GB834163A
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Publication of GB1014911A publication Critical patent/GB1014911A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D213/04—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 having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—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 having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton

Abstract

Isocyanides of the formula R-N­C, in which R is a substituted or unsubstituted alkyl, aryl, aralkyl, alkaryl or heterocyclic radical are made by reacting at - 50 DEG to + 100 DEG C., one equivalent of thioformamide R-NH-CHS in an organic solvent, preferably methylene chloride with no added water at the beginning of the reaction, with two or more equivalents of an inorganic or tertiary organic base, preferably an alkali metal alkoxide or hydroxide or triethylamine, and at least half an equivalent of organic or inorganic acylating agent defined as phosgene, phosphorus halides or oxyhalides, aryl sulphonic halides, trifluoroacetic anhydride cyanogen halides cyanuric halides, 2,4-dinitrochlorobenzene, picryl chloride, and N-acetyl-N,N1-dicyclohexyl chloroformamide, especially cyanogen chloride, the molar amount of acylating agent being less than one half the molar amount of base. If the starting material is optically active, the optical activity will be preserved in the product. Named starting materials include 1-diethyl-N-thioformyl-glutamate, N-thioformyl-valyl-glycine ethyl ester, N - thioformyl - glycol - a - hydroxy - valeroyl - glycine-t-buty ester, 2,4-dimethoxy-5-chlorothioformanilide. The examples describe, using cyanogen bromide, triethylamine as reagents in methylene chloride, the preparation of phenyl isocyanide, 1-a -isocyano isovaleric acid methyl ester (optically active), a -isocyano-propionyl-sarcosyl-glycine-t-butyl ester. a -Isocyano-isovaleroyl - glycolyl - glycine - t - butyl ester, 2,4-dimethoxy - 5 - chloro - phenyl - isocyanide was obtained using picryl chloride in place of cyanogen bromide.
GB834163A 1962-03-02 1963-03-01 Process for the production of isonitriles Expired GB1014911A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF36166A DE1158499B (en) 1962-03-02 1962-03-02 Process for the production of isonitriles

Publications (1)

Publication Number Publication Date
GB1014911A true GB1014911A (en) 1965-12-31

Family

ID=7096339

Family Applications (1)

Application Number Title Priority Date Filing Date
GB834163A Expired GB1014911A (en) 1962-03-02 1963-03-01 Process for the production of isonitriles

Country Status (2)

Country Link
DE (1) DE1158499B (en)
GB (1) GB1014911A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2511261A1 (en) * 2011-04-05 2012-10-17 Duquesne University Of The Holy Ghost Composition, synthesis and use of isonitriles

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE59810678D1 (en) * 1997-07-25 2004-03-04 Ugichem Gmbh ISOCYANOALKYL CARBONIC DERIVATIVES, THEIR IMPLEMENTATION IN ISOCYANID MULTICOMPONENT REACTIONS TO SEK.AMIDOALKYL CARBONIC DERIVATIVES AND THESE SEK.AMIDOALKYL CARBONIC DERIVATIVES
DE19732176A1 (en) * 1997-07-25 1999-01-28 Ivar Ugi Isocyano-ethyl and isocyano-propyl carbonate ester compound(s)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2511261A1 (en) * 2011-04-05 2012-10-17 Duquesne University Of The Holy Ghost Composition, synthesis and use of isonitriles

Also Published As

Publication number Publication date
DE1158499B (en) 1963-12-05

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