A general, facile, and safe procedure for the preparation of S-methyl N-alkylthiocarbamates by methylthiocarbonylation of primary aliphatic amines with S,S-dimethyl dithiocarbonate

Article abstract of DOI:10.1055/s-2007-965943

A general procedure is reported for the selective preparation of S-methyl N-alkylthiocarbamates by methylthiocarbonylation of primary aliphatic amines, employing S,S-dimethyl dithiocarbonate as a phosgene substitute. The reactions are carried out in water at room temperature (20-25°C), with S,S-dimethyl dithiocarbonate/amine ratios varying between 1:1.2 and 1:2, and with quantitative recovery of the excess amine. The target products are obtained in exceptionally high yields (generally >95%) and with very high purity (generally >99.5%). Also to be noted is the complete chemoselectivity of the reactions, which can be carried out in the presence of hydroxy or aminophenyl groups. Georg Thieme Verlag Stuttgart.