N, N- bis (2-CHLOROETHYL)AMIDES AND N, N- bis (2-CHLOROETHYL)HYDRAZIDES OF CARBOXYLIC ACIDS OF THE FURAN SERIES

Abstract

Reaction of N, N-bis(2-chloroethyl)amine hydrochloride with chloroanhydrides of carboxylic acids of the furan series, in chloroform in the presence of pyridine gives N, N-bis(2-chloroethyl)amides of furan carboxylic acid, furylacrylic acid, 5-nitrofuran carboxylic acid, and 5-nitrofurylacrylic acid. N, N-bis(2-chloroethyl)hydrazides of furan carboxylic acid, furyl carboxylic acid, 5-nitrofuran carboxylic acid, and 5-nitrofurylacrylic acid were obtained in 78–88% yields by reacting N, N-bis(2-chloroethyl)hydrazine hydrochloride with the chloroanhydrides of the appropriate acids in chloroform in the presence of pyridine. The last two hydrazides were prepared in 31 % and 56 % yield, respectively, using anhydrous sodium acetate in place of pyridine. Authors: B. V. Kurgan, S. A. Giller, A. A. Gruze. English Translation in Chemistry of Heterocyclic Compounds , 1965, 1 (1), pp 5-7 http://link.springer.com/article/10.1007/BF01168908