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Molecules 2009, 14(11), 4634-4643; doi:10.3390/molecules14114634

3-(2-Aminophenyl)-4-methyl-1,3-thiazole-2(3H)-thione as an Ecofriendly Sulphur Transfer Agent to Prepare Alkanethiols in High Yield and High Purity

Laboratoire de synthèse organique appliquée, Département de Chimie, Faculté de Sciences, Université d’Oran-es-Senia, Algeria
ISM2, Chirosciences, Université Paul Cézanne Aix-Marseille III, 13397 Marseille CEDEX 20, France
Author to whom correspondence should be addressed.
Received: 29 October 2009 / Revised: 10 November 2009 / Accepted: 11 November 2009 / Published: 12 November 2009
(This article belongs to the Special Issue Advances in Heteroaromatic Chemistry)
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A new process is described for preparing very pure linear alkanethiols and linear α,ω-alkanedithiols using a sequential alkylation of the title compound, followed by a ring closure to quantitatively give the corresponding 3-methyl[1,3]thiazolo[3,2-a]-[3,1]benzimidazol-9-ium salt and the alkanethiol derivative under mild conditions. The alkanethiol and the heteroaromatic salt are easily separated by a simple extraction process. The intermediate thiazolium quaternary salts resulting from the first reaction step can be isolated in quantitative yields, affording an odourless protected form of the thiols.
Keywords: thiols; dithiols; sulphur transfer; thiazoline-2-thione thiols; dithiols; sulphur transfer; thiazoline-2-thione
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Mehdid, M.A.; Djafri, A.; Roussel, C.; Andreoli, F. 3-(2-Aminophenyl)-4-methyl-1,3-thiazole-2(3H)-thione as an Ecofriendly Sulphur Transfer Agent to Prepare Alkanethiols in High Yield and High Purity. Molecules 2009, 14, 4634-4643.

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