Triethylamine → N-methoxy N-methyl 2-(phenylthio)-benzamide

Participants

Reaction Steps

A solution of 3.7 parts of 2-(phenylthio)-benzoylchloride in 50 parts of tetrahydrofuran was added to a cold (~5°) stirred solution of 1 part N,O-dimethyl hydroxylamine and 1.6 parts triethylamine in 75 parts of tetrahydrofuran. The mixture was stirred for 8 hrs. and the temperature was allowed to rise to room temperature. Removal of the precipitated triethylamine hydrochloride by filtration and concentration of the filtrate under vacuum gave 3.3 parts of N-methoxy N-methyl 2-(phenylthio)-benzamide as a very viscous oil. NMR (CDCl3) 3.3δ(S,3H,N-CH3), 3.5δ(S,3H,-O-CH3), 7.3δ(m,9H,Aromatic H).

Provenance & Evidence