首页|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

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

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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 degrees 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.

thiocarbamatesthiocarbonylationdithiocarbonatesamineschemoselectivityCARBON-MONOXIDESS-DIALKYL DITHIOCARBONATESASSISTED CARBONYLATIONUREA DIPEPTIDESALLYLIC THIOLSALKYL-HALIDESSULFURCONVERSIONCARBONIMIDODITHIOATESREARRANGEMENT

Artuso E、Carvoli G、Degani I、Fochi R、Magistris C

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Univ Turin, Dipartimento Chim Gen & Organ Applicata, I-10125 Turin, Italy

Oxon Italia SpA, I-20016 Pero, Milano, Italy

2007

Synthesis

Synthesis

ISSN:0039-7881
年,卷(期):2007.(7)