GB1014911A - Process for the production of isonitriles - Google Patents
Process for the production of isonitrilesInfo
- 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
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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.
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)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2210795T3 (en) | 1997-07-25 | 2004-07-01 | Ugichem Gmbh | DERIVATIVES OF ISOCIANO-ALQUIL-CARBONIC ACIDS, ITS CHEMICAL CONVERSION IN REACTIONS OF MULTIPLE COMPONENTS WITH AN ISOCIANURE TO GIVE DERIVATIVES OF SEC.AMIDO-ALQUIL-CARBONIC ACIDS, AND THESE DERIVATIVES OF SE.AMIDO-ALIC. |
DE19732176A1 (en) * | 1997-07-25 | 1999-01-28 | Ivar Ugi | Isocyano-ethyl and isocyano-propyl carbonate ester compound(s) |
-
1962
- 1962-03-02 DE DEF36166A patent/DE1158499B/en active Pending
-
1963
- 1963-03-01 GB GB834163A patent/GB1014911A/en not_active Expired
Cited By (1)
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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