A STUDY OF THE REACTIONS OF AMMONIUM SULPHAMATE WITH AMIDES AND UREAS

Abstract

The preparation of nitriles from amides and ammonium sulphamate was investigated. The method was found to be generally applicable and good yields were obtained in most cases. The mechanism of the reaction involved the liberation of ammonia and the formation of ammonium N-carbonyl sulphamates, which decomposed into nitriles and ammonium bisulphate.The mechanism for the formation of guanidine and cyanuric acid from ureas was elucidated. The effects of methyl, phenyl, acetyl, and benzoyl groups on the reactivity of the urea molecule were determined. Methylamine and aniline were obtained from methylurea and phenylurea together with guanidine and cyanuric acid. Acetylurea and benzoylurea formed acetonitrile and benzonitrile, the yield of guanidine being low but that of cyanuric acid very high.