Synthesis of benzenesulfonamide serinol by the Hinsberg reaction

Abstract

This research focused on synthesising benzenesulfonamide serinol (BSSe), a new sulfonamide monomer, by the Hinsberg reaction between primary amine of serinol and sulfonyl of benzenesulfonyl chloride (BSC) in an alkaline environment. The effect of the reacted environment on the reaction efficiency and structure of BSSe were investigated. The results of the Proton nuclear magnetic resonance (H¹NMR) spectroscopy and Fourier transform infrared (FTIR) spectroscopy indicated that the BSSe was successfully synthesised through the appearance new peak of sulfonamide, characterised by secondary amines.  The highest reaction efficiency of BSSe was 14.51% at a reaction time of 22 hours, the mol ratio of BSC/1.4-dioxane was 1/10, the concentration of NaOH solution was 1 M. The BSSe molecule contained the sulfonamide group and a couple of hydroxyl groups, which were able to copolymerise easily with other monomers or polymers. BSSe was oriented to synthesise copolymer for pH-sensitive hydrogel in the drug delivery system.