One-Pot, Three-Step Preparation of Alkyl and Aryl Alkylcarbamates from S-Methyl N-Alkylthiocarbamates

Abstract

A general procedure for the synthesis of alkyl and aryl alkylcarbamates starting from the corresponding S-methyl N-alkyl­thiocarbamates is described. This procedure consists of three steps that are carried out in a one-pot fashion, without isolating the intermediate N-alkylcarbamoyl chlorides or alkyl isocyanates. All the target products were obtained in high yields (16 examples, average yield 91%). To be noted is the recovery of a co-product of industrial interest, dimethyl disulfide, in a half mole amount for each mole of thiocarbamate, with complete exploitation of the reagent. The alkyl isocyanates, if required, can also be isolated in high yields.

Key words

carbamates - amines - dithiocarbonates - thiocarbamates - isocyanates

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1

Professor Emeritus, University of Turin (Italy).

12

Oxon Italia S.p.A., 20016 Pero (Milano), Italy.

16

Spectral Data Base for Organic Compounds SDBS (National Institute of Advanced Industrial Science and Technology). SDBS Web: http://riodb.ibase.aist.go.jp/index.html.

17

Details are reported in reference 4a.