Raiford and Shelton [J. Org. Chem., 4, 207 (1939)] found that hot pyridine causes 2-carbophenoxyamino-4-methy 1-6-bromophenyl p-tolylsulfonate to lose phenol and give a "condensation product" which was found to be a 1,3- derivative of uretedione (uretidone). This type of derivative was also obtained by Warren and Wilson [Ber., 68, 957 (1935) J by the action of thionyl chloride on phenylurethane. But it has now been found that the last-named reaction is specific for phenylure thane. When the phenyl radical contains a "negative" substituent, thionyl chloride causes no action after five hours refluxing. If the substituent is alkyl the treatment causes tar formation, from which nothing definite could be isolated. Ethyl and n-butyl carbamates react with thionyl chloride to give the corresponding esters of allophanic acid and small amounts of cyanuric acid. Under the same treatment 2-naphthylurethane undergoes chlorination to give the 1-chloro derivative, while the 1-naphthyl compound gives the 4-chloro derivative.
Proceedings of the Iowa Academy of Science
© Copyright 1941 by the Iowa Academy of Science, Inc.
Freyermuth, H. B. and Raiford, L. Chas.
"Action of Thionyl Chloride on Urethanes (Abstract),"
Proceedings of the Iowa Academy of Science, 48(1), 248-248.
Available at: https://scholarworks.uni.edu/pias/vol48/iss1/49