Preparation of Sulfonamides from Sodium Sulfonates: Ph3P ⋅ Br2 and Ph3P ⋅ Cl2 as a Mild Halogenating Reagent for Sulfonyl Bromides and Sulfonyl Chlorides

Tadashi Kataoka; Tetsuo Iwama; Tomofumi Setta; Atsuko Takagi

doi:10.1055/s-1998-4488

Synthesis 1998; 1998(4): 423-426
DOI: 10.1055/s-1998-4488

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Preparation of Sulfonamides from Sodium Sulfonates: Ph₃P ⋅ Br₂ and Ph₃P ⋅ Cl₂ as a Mild Halogenating Reagent for Sulfonyl Bromides and Sulfonyl Chlorides

Tadashi Kataoka^* , Tetsuo Iwama, Tomofumi Setta, Atsuko Takagi

^*Gifu Pharmaceutical University, 6-1, Mitahora-higashi 5-chome, Gifu 502, Japan; Fax + 81(58)2 37 59 79; E-mail: kataoka@gifu-pu.ac.jp

Abstract

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Arene- and alkanesulfonamides were prepared by treatment of the corresponding sodium sulfonates with triphenylphosphine dibromide or dichloride followed by amines in the presence of triethylamine via sulfonyl halides. Reactions of sodium aminosulfonates gave cyclized products. Amidation of p-toluenesulfonic acid with triphenylphosphine dichloride was also examined to give N-benzyl-p-toluenesulfonamide. Methyl p-toluenesulfonate was obtained by esterification of sodium p-toluenesulfonate via p-toluenesulfonyl chloride.

triphenylphosphine dihalide - halogenation - sodium sulfonate - sulfonamide - sultam

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