Facile conversion of carboxamides to nitriles

✍ Scribed by Khuong Mai; Ghanshyam Patil

• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 268 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)84487-1

✦ Synopsis

Alkyl, aralkyl, aryl, heteroaryl carboxamides bearing various functionalities are readily converted to the corresponding nitriles in good yields using the liquid "diphosgene", trichloromethyl chloroformate, as dehydrating agent. In many cases, the procedure does not require extraction, and hence offers a very simple work-up. The preparation of nitriles by the dehydration of carboxamides is very well documented.1-24 Certain amides have been converted to nitriles with the basic reagents, where relative drastic conditions have been employed. l-4 Some examples have involved mesitamide with sodium hydroxide in refluxing ethylene glycol,l benzamide with "deficient" amount of lithium aluminum hydride,2 phenylacetamide with 3.3 equivalents of n-butyl lithium,3 and benzamide with silazanes at 220' for several hours.4 On the other hand acidic reagents appear to offer milder conditions and better yields: Trichloroacetyl chloride,5 ethyl polyphosphate,6 trimethylsilyl polyphosphate,7 cyanuric chloride/dimethylformamide,