Previous work in this laboratory has shown that when N-n-buty 1-N -chloro-p-toluenesulfonamide, N-n-butyl-N-chloroacetamide, or N-n-butyl-N-chloropropionamide is dissolved in sulfuric acid and heated, ring closure occurs with the formation of pyrrolidine in good yields. It was thought that N, N'-di-n-butyl-N, N'- dichlorourea might react in a similar manner. This was found to be the case. When this compound was dissolved in 95 per cent sulfuric acid and heated for a period of one hour at 120-130° C. pyrrolidine was formed in yields of 50 to 55 per cent. Under similar conditions N, N-dimethyl-N'-n-butyl-N'-chlorourea gave pyrrolidine in yields of 5 to 10 per cent.
Proceedings of the Iowa Academy of Science
© Copyright 1941 by the Iowa Academy of Science, Inc.
Coleman, George H. and Alliger, Glen
"Pyrrolidine from N-alkyl-N-Chloroureas (Abstract),"
Proceedings of the Iowa Academy of Science: Vol. 48:
, Article 46.
Available at: https://scholarworks.uni.edu/pias/vol48/iss1/46