Process for the preparation of thiophenols

Details Process for the preparation of thiophenols Process for the preparation of thiophenols

C - Chemistry, Metallurgy

07

C

C07C 319/02 (2006.01) C07C 321/26 (2006.01) C07C 323/62 (2006.01)

Patent

CA 2423300

The invention provides a process for preparation of a thiophenol of formula I (see formula 1) wherein n is an integer from 1 to 5 and R is hydrogen, alkyl, hydroxyalkyl, alkylamino, dialkylamino, alkenyl, alkynyl, alkoxy, alkylthio, phenyl, naphthyl, phenoxy, phenylthio, halogen, hydroxy, mercapto, carboxyl, sulfo, or heterocyclyl, by reacting a phenyldiazonium salt of formula II (see formula 2) wherein n and R are as defined for the thiophenol of formula I and X is halogen or hydrogen sulphate, with 1.2 to 5 mol of sulfur powder per mol of the phenyldiazonium salt of formula II, at a temperature in the range of 20 to 100°C, in the presence of 2.5 to 5 mol per mol of the phenyldiazonium salt of formula II of an aqueous base that is an alkali or alkaline earth metal hydroxide or ammonia, converting the excess of sulfur into water soluble thiosulfate by adding of sodium sulfite, sodium hydrogen sulfite or sulfur dioxide, acidifying the reaction solution, and isolating the thiophenol of formula I.

L'invention concerne un procédé relatif à l'élaboration de thiophénols de formule (I). Dans ladite formule, n est un entier compris entre 1 et 5, et R est hydrogène, alkyle, hydroxyalkyle, alkylamino, dialkylamino, alcényle, alkynyle, alcoxy, alkylthio, phényle, naphthyle, phénoxy, phénylthio, halogène, hydroxy, mercapto, carboxyle, sulfo ou hétérocyclyle. On fait réagir des sels de phényldiazonium de formule (II) (n et R sont tels que définis, et X est halogène ou sulfate d'hydrogène) avec du soufre, sous température élevée, en présence d'une base aqueuse, puis on isole les composés de formule (I).

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