Preparation of some N,N' -Diacyl-4-imidazolines

Abstract

The oxidation of benzhydrazide to benzoic acid was studied as a model reaction for the conversion of acid hydrazides to their corresponding carboxylic acids. This oxidation was carried out with iodine using both ether - aqueous sodium carbonate and ethyl acetate-aqueous sodium carbonate as media.

Four new N, N'-diacyl-4-imidazolines were prepared by catalytic hydrogenation of imidazole with platinum oxide in the presence of the corresponding acid anhydrides. The compounds prepared were N,N'-dipropionyl-4-imidazoline, N,N'-dibutyryl-4-imidazoline, N,N'-dipentanoyl-4-imidazoline and N,N'-dihexanoyl-4-imidazoline. The ultra-violet, infra-red and nuclear magnetic resonance spectra of these compounds were determined. When 1-acetylimidazole was reduced with the aforementioned catalyst in propionic anhydride, the product was not the mixed imidazoline but N,N'-dipropionyl-4-imidazoline. Unlike the corresponding N,N'-diacylimidazolidines previously studied, the four N,N'-diacyl-4-imidazolines did not show antimycotic activity against Aspergillus flavus.