Polystyrene supported N-alkyl-N-acyl sulfonamide resins (5) were prepared through a two-step modification reaction on polymer beads and developed as an effective type of recyclable solid-phase reagents. Polystyrene sulfonyl chloride (1) reacted with primary amines (2) to afford supported N-alkyl sulfonamide resins (3), and the resin 3 was acylated using either acyl chloride 4 or acidic anhydride in pyridine to afford the resins 5. Reaction of the acylated sulfonamide resins 5 as acyl transfer reagents with nucleophilic amines yielded the secondary amides. It was found that the substituents of N-alkyl(R¹)-N-acyl(R²CO) sulfonamide resins had significant influences on the acyl transfer reaction. According to the acyl transfer reactivity of N-alkyl-N-acyl sulfonamide resins (5), alkyl group R¹ was ordered as follows: phenyl＞benzyl＞methyl＞n-butyl＞＞H, and R²CO: p-nitrobenzoyl＞benzoyl＞acetyl. The nucleophilic ability of the amines had effect on the yields of the amides as well. The N-phenyl-N-benzoyl sulfonamide resin (5hb) was found to be regenerated three times without loss of their activity.

Key words: polystyryl N-alkyl sulfonamide resin, polystyrene-supported N-alkyl-N-acyl sulfonamide resin, polymeric acyl transfer reagent, synthesis of secondary amide