Reaction between toluene-p-sulphonamide and formaldehyde

Abstract

Three pure compounds present in toluene-p-sulphonamide–formaldehyde resins have been prepared and identified. Toluene-p-sulphonamide, when treated with formalin under neutral or alkaline conditions, gave bis-(p-tolyl-sulphonamido)methane (III). The intermediate hydroxymethyl compound was not isolated, presumably because it was too reactive. Condensation with acidic formalin or trioxan gave only 1,3,5-tris-(p-tolylsulphonyl)hexahydro-1,3,5-triazine (I). The reaction of toluene-p-sulphonyl chloride with hexamethylenetetramine yielded 3,7-bis-(p-tolylsulphonyl)-1,3,5,7-tetra-azabicyclo[3,3,1]nonane (II).