Mild and safer preparative method for nonsymmetrical sulfamides via N-sulfamoyloxazolidinone derivatives: Electronic effects affect the transsulfamoylation reactivity

Borghese, A.;Antoine, L.;Van Hoeck, J. P.;Mockel, A.;Merschaert, A.
(2006) Organic Process Research and Development — Vol. 10, n° 4, p. 770-775 (2006)

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Authors
  • Borghese, A.
    Author
  • Antoine, L.
    Author
  • Van Hoeck, J. P.
    Author
  • Mockel, A.
    Author
  • Merschaert, A.
    Author
Abstract
Sulfamides (R1R2N-SO2-NR3R4) are traditionally prepared by using strong electrophilic and hazardous reagents such as N-sulfamoyl chloride, sulfonyl chloride, phosphorus oxychloride, or phosphorus pentachloride. We report here a safer and more convenient synthetic methodology for large-scale preparation of sulfamides using the N-substituted oxazolidin-2-one derivatives 5 as synthetic equivalent of the corrosive and hazardous N-sulfamoyl chloride. The scope of the use of N-sulfamoyloxazolidinones to prepare nonsymmetrical sulfamides is explored.
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Borghese, A., Antoine, L., Van Hoeck, J. P., Mockel, A., & Merschaert, A. (2006). Mild and safer preparative method for nonsymmetrical sulfamides via N-sulfamoyloxazolidinone derivatives: Electronic effects affect the transsulfamoylation reactivity. Organic Process Research and Development, 10(4), 770-775. https://doi.org/10.1021/op0600106 (Original work published 2006)