Aqueous ring opening of N-tosylaziridine with aniline derivatives

A series of N-(p-X-phenyl)-N′-(p-toluenesulfonyl)1,2-ethylenediamines compounds, TsN(H)CH2CH2N(H)PhX, were synthesized by the uncatalyzed ring opening reaction of N-tosylaziridine with p-X-aniline derivatives in pure water at 50 °C. No solvolysis product was observed and the only side product was that of a subsequent ring opening reactions of N-tosylaziridine with the product anilines leading to substituted diethylenetriamines, XPhN(CH2CH2NTs)2.