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
©1941 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