Process for the preparation of 4-methyl-5-(2-chloroethyl)-thiazole and analogues thereof

摘要

The present invention relates to a process for the preparation of compounds of general formula (I), wherein R stands for a straight chained C1-5alkyl group substituted by a chlorine atom in the 2-position, and acid addition salts thereof, characterized by reacting a 3,5-dichloro-2-alkanone of general formula (V), wherein R is a defined above, with an inorganic thiocyamate, and a) converting the 3-thiocyanato-5-chloro-2-alkanone of general formula (IV), thus obtained, wherein R is as defined above, into 2-chloro-4-methyl-5-(2-chloroalkyl)-thiazole of general formula (II), wherein R is as defined above, by gaseous hydrochloric acid in an organic solvent, hydrogenating the said compound in the presence of a metal catalyst in an organic solvent, or b) reacting said compound of general formula (IV) with an aqueous mineral acid and treating the 2-hydroxy-4-methyl-5-(2-chloroalkyl)-thiazole of general formula (III), thus obtained with a halogenating agent, and hydrogenating the 2-chloro-4-methyl-5-(2-chloroalkyl)-thiazole of general formula (II) thus obtained, wherein R is as defined above, in an organic solvent in presence of a metal catalyst, and optionally converting the 4-methyl-5-(2-chloroalkyl)-thiazole of general formula (I), wherein R is as defined above, thus obtained or a hydrochloride salt thereof, in a manner known per into another acid addition salt or setting free a compound of general formula (I), wherein R is a defined above, from its acid addition salt.