Synthesis 2008(10): 1612-1618  
DOI: 10.1055/s-2008-1072573
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Emma Artuso, Iacopo Degani, Rita Fochi*, Claudio Magistris
Dipartimento di Chimica Generale e Chimica Organica, Università degli Studi di Torino, C.so M. D’Azeglio 48, 10125 Torino, Italy
Fax: +39(011)6707642; e-Mail: rita.fochi@unito.it;
Further Information

Publication History

Received 30 January 2008
Publication Date:
27 March 2008 (online)

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.

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1

Professor Emeritus, University of Turin (Italy).

12

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

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