Process for preparing basic thioethers and the salts thereof

Details Process for preparing basic thioethers and the salts thereof Process for preparing basic thioethers and the salts thereof

C - Chemistry, Metallurgy

07

D

260/367.3

C07D 307/52 (2006.01) A61K 31/34 (2006.01) A61K 31/35 (2006.01) C07D 307/54 (2006.01)

Patent

CA 1279328

ABSTRACT OF THE DISCLOSURE The invention provides a process for preparing the hydrochloride of 1-{2-[5-dimethylaminomethyl-2-(furylmethylthio)- ethyl]}-amino-1-methylamino-2-nitroethylene of formula (I) and, if desired, for transforming this compound to the base of formula (I), which comprises a) reacting the monohydrochloride of 2-[(2- aminoethyl)-ethiomethyl]-5-dimethylaminomethylfuran of formula (II) with 1-methylthio-1-methylamino-2-nitroethylene of formula (III) optionally in the presence of water and/or of an organic solvent, or b) reacting the hydrochloride of 5-dimethylamino- methy1-2-furfuryl alcohol of formula (IV) with cysteamine hydro- chloride at a temperature between 20 and 120°C without adding a solvent. In the presence of a catalytic amount of a mineral acid, or in the presence of a catalytic amount of a substance furnish- ing a mineral acid, then, if desired, separating the obtained dihydrochloride of the base of formula (II) and/or liberating therefrom the monohydrochloride of the base of formula (II) and reacting optionally without separating it with 1-methylthio-1- methylamino-2-nitroethylene of the formula (III) and, if desired, separating and purifying the hydrochloride of the base of formula (I) and/or, if desired, liberating therefrom the base of formula (I) and/or, if desired, purifying and transforming it to the hydrochloride thereof. The invention also provides as inter- mediates in the process 2-[(2-aminoethyl)-thiomethyl]-5-dimethyl- aminomethylfuran dihydrochloride or 2-[(2-aminoethyl)-thiomethyl] -5-dimethylaminomethylfuran monohydrochloride.

458870

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