Alkyl- and Arylamination of Arenesulfonates by Sodium Hydride and Aminest

Abstract

By the reaction of potassium 1-naphthalenesulfonate with 2.4-fold moles of sodium hydride in butylamine at 140°C for 7 hours, N-butyl-1-naphthylamine was obtained in a 86% yield, accompanied with naphthalene, 1-naphthylamine and dibutylamine as by-products. Various arenesulfonates with sodium hydride in alkylamines (R =Et, Pr, Bu, cyclohexyl) or arylamines (Ar = Ph, p-tolyl) gave the corresponding N-alkylarylamines or diarylamines in good yields. In contrasts to the alkylamination, no aromatic hydrocarbon was formed by the arylamination. Arenesulfonates with sodium hydride in ethylenediamine gave N-arylethylenediamines.