Reactivity of 2-Sulfobenzoic Acid Imide and Benzenesulfonamide in Arenesulfonylation

Abstract

Experimental study of the kinetics of the reactions of 2-sulfobenzoic acid imide (saccharin) and benzenesulfonamide with 3-nitrobenzenesulfonyl chloride in a 1,4-dioxane-water mixture (80:20 by weight) in the temperature range 298–318 K has shown that both compounds are low reactive (k₂₉₈ = 1.66 × 10⁻⁴ and 3.37 × 10⁻³ L mol⁻¹ s⁻¹, respectively). The activation barriers to these reactions exceed 50 kJ/mol. Aqueous dioxane can be recommended as a solvent for the preparation of N-(benzenesulfonyl)-3-nitrobenzenesulfonamide in up to 87% yield.