Synthesis of Poly(p-Benzenesulphonamide) Part I. Preparation of Sulphanilic Acid Derivatives for Use as Intermediates

In view of the unique properties of poly (p-benzamide), particularly as a fibre, the synthesis of the structurally related poly (p-benzenesulphonamide) has been investigated. This first paper describes the preparation of two groups of possible precursors of the polymer starting with sulphanilic acid. The first group includes N-sulphinylaniline-4-sulphochloride, aniline-4-sulphochloride hydrochloride and aniline-4-sulphochloride. The key to the synthesis of these intermediates is the conversion of sulphanilic acid to N-sulphinylaniline-4-sulphochloride by reaction with thionyl chloride in the presence of a catalytic amount of dimethyl formamide. For the synthesis of poly (N-methyl-benzenesulphonamide), N-methylsulphanilic acid has been converted into N-methylaniline-4-sulphochloride hydrochloride by treatment with thionyl chloride. Some N-acetylated sulphanilic acid derivatives, CH₃CONH-C₆H₄-SO₂X, where X?OH, OEt, OC₆H₅ and Cl, and N-acetyl-1-naphthylamine-4-sulphochloride have also been prepared for evaluation as monomers in the synthesis of polysulphonamides by melt polymerisation.