Triethylamine → N-methyl-2-(4-amino-3-tert-butyl-5-methylphenylthio)succinimide

Participants

Reaction Steps

A stirred solution of 1.0 g (5 mmol) of 2-tert-butyl-4-mercapto-6-methylaniline, 0.6 g (5 mmol) of N-methylmaleimide and 0.1 g (1 mmol) of triethylamine in 10 mL of toluene is heated at 50° C. for 18 hours. The solvent is removed in vacuo and the residue is purified by flash chromatography (silica gel, 3:2, heptane:ethyl acetate eluent) followed by recrystallization from a heptane:toluene solvent mixture to give 0.8 g (51%) of the title compound as a white solid melting at 92°-94° C. 1HNMR (CDCl3) (90 MHz) 1.37 (s, 9H), 2.08 (s, 3H), 2.66 (dd, 1H), 3.06 (dd, 1H), 2.80 (s, 3H) 3.82 (dd, 1H) 4.02 (exchangeable s, 2H), 7.15 (meta d, 2H).

Provenance & Evidence