A study of mono-, di- and tri-tosylated amines: An unexpected sulfonamide

2-Aminobenzylaniline was ditosylated and gave an unexpected product N,N-ditosylamino-2-benzylaminobenzene in which the primary amine had ditosylated, and the benzylamine was unreacted. The benzylamine, although more electron rich, is sterically crowded and less nucleophilic than the primary amine in this ditosylated system. Sterically crowded tosylamides were prepared by reacting o-phenylenediamine, p-phenylenediamine and 1,8-diaminonaphthalene with tosyl chloride.