Acid-promoted reaction of N-(cyanomethyl) amide with nitrosation reagent: Facile synthesis of 1,2,4-oxadiazole-3-carboxamide

Abstract 1,2,4-Oxadiazole-3-carboxamide has been extensively used in the pharmaceutical chemistry. In this study, 1,2,4-oxadiazole-3-carboxamide is accomplished through an acid-promoted reaction of N-(cyanomethyl)amide with nitrosation reagent. This novel preparation of 1,2,4-oxadiazole-3-carboxamide was carried out at 25 °C, and the yield of target compounds was as high as 92%. At the same time, the amount of acid used is reduced. A mechanism speculation for the formation of 1,2,4-oxadiazole-3-carboxamide has been provided. The new synthetic method provides great convenience for the synthesis of compounds containing 1,2,4-oxadiazole-3-carboxamide.