Abstract
The reaction of N-phenylsulfonylbenzoxazolone with amines was investigated in order to study the mechanism of the reaction between aryloxazolones and amines. The sulfonyl group accelerates the reaction considerably. The structure of 2-(phenylsulfamido)phenyl esters of the corresponding N-substituted carbamic acids was assigned to the products on the basis of the IR spectra and alternative synthesis. The reaction with secondary aliphatic amines (dimethyl- and diethylamine)proceeds considerably more slowly and results in the formation of 2-(phenylsulfamido)phenol.
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D. Simov, V. Kalčeva, M. Arnaudov, and B. Galabov, C. r. Acad. Bulg. Sci., 21, 877 (1968).
D. Simov and V. Kalčeva, C. r. Acad. Bulg. Sci., 17, 825 (1964).
D. Simov and V. Kalčeva, Godishnik na SU “K. Okhridski,” 61, 155 (1966/1967).
L. Bellamy, Infrared Spectra of Complex Molecules, Methuen (1958).
H. Zinner and H. Herbig, Ber., 88, 693 (1955).
T. Davis and K. Blanchard, J. Am. Chem. Soc., 45, 1819 (1923).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1333–1336, October, 1971.
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Kalčeva, V., Simov, D. Reaction of N-phenylsulfonylbenzoxazolone with some amines. Chem Heterocycl Compd 7, 1245–1248 (1971). https://doi.org/10.1007/BF00479940
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DOI: https://doi.org/10.1007/BF00479940