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MethylN-(benzylsulfonyl)oxamate as a probable intermediate in the synthesis of 4-hydroxy-5-phenyl-3(2H)-isothiazolone 1,1-dioxide from phenylmethanesulfamide and dimethyl oxalate in the presence of bases

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Abstract

The formation of 4-hydroxy-5-phenyl-3(2H)-isothiazolone 1,1-dioxide from phenylmethanesulfamide and dimethyl oxalate under the action of bases is apparently a two-stage process involving the formation of linear methylN-(benzylsulfonyl)oxamate followed by its cyclization. A stable complex of the heterocycle with dimethylformamide was synthesized.

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References

  1. C. S. Rooney, D. W. Cohran, C. Ziegler, E. J. Cragoe, and H. W. R. Williams,J. Org. Chem., 1984,49 (12), 2212.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation

    S. G. Zlotin & A. I. Gerasyuto

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  1. S. G. Zlotin
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  2. A. I. Gerasyuto
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 396–398, February, 1999.

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Zlotin, S.G., Gerasyuto, A.I. MethylN-(benzylsulfonyl)oxamate as a probable intermediate in the synthesis of 4-hydroxy-5-phenyl-3(2H)-isothiazolone 1,1-dioxide from phenylmethanesulfamide and dimethyl oxalate in the presence of bases. Russ Chem Bull 48, 394–395 (1999). https://doi.org/10.1007/BF02494576

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  • DOI: https://doi.org/10.1007/BF02494576

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