Dimethylamine → S-2-[4-(1-methylpropoxy)phenoxy]ethyl N,N-dimethylthiocarbamate

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Reaction Steps

Following procedure C in H. Tilles, JACS 81:714 (1959) a solution of dimethylamine (0.58 ml, 8.79 mmol) and triethylamine (1.22 ml, 8.79 mmol) in 3 ml of t-butyl alcohol is cooled to 15°, after which carbonylsulfide (0.71 g, 11.87 mmol) is passed in with vigorous stirring. The solution is then warmed to 30°, with stirring, and 2-[4-(1-methylpropoxy)phenoxy]ethyl bromide (2.40 g, 8.79 mmol) is added rapidly. The reaction mixture is heated slowly to 50° and maintained at 50° for 3 hours. The solvent is then distilled off and the product is worked up to give S-2-[4-(1-methylpropoxy)phenoxy]ethyl N,N-dimethylthiocarbamate (compound 36, Table B).

Provenance & Evidence