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Synthesis 2008(18): 2919-2924  
DOI: 10.1055/s-2008-1067233
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Easy and Efficient One-Step Procedure for the Preparation of Alkyl and Aryl Alkylcarbamates from S-Methyl N-Alkylthiocarbamates

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
e-Mail: rita.fochi@unito.it;
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Publication History

Received 29 April 2008
Publication Date:
22 August 2008 (online)

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Abstract

A general, one-step procedure for the synthesis of alkyl and aryl alkylcarbamates, by the direct reaction of S-methyl N-alkyl­thiocarbamates with alcohols or phenols in toluene at reflux in the presence of triethylamine, is reported. All the target products were obtained in high yield (15 examples, average yield 94%) and very high purity (>99.2%). The recovery of a co-product of industrial interest, methanethiol, in an amount of one mole for each mole of thiocarbamate, with complete exploitation of the reagent, should also be noted.

Key words

carbamates - thiocarbamates - S,S-dimethyl dithiocarbonate - green chemistry

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1

Professor Emeritus, University of Turin (Italy).

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For details, see IT patent application pending: Carvoli, G.; Degani, I.; Pallucca, E.; Fochi, R.; Gazzetto, S.; Artuso, E.; Lazzaroni, M.; Cadamuro, S. Oxon Italia S.p.A. Italy, patent request No. MI 2005 001284, 2005.

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