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

• Main Authors: ILDIKO BUTTKAI, MIHALY SUTO, CSABA HUSZAR, IDA SZVOBODA, ARPAD KOVARI, FERENC MORASZ, ERZSEBET SZALAY, KAROLY BAN, PETER GYORI, ENDRE PALOSI, GERGELY HEJA, PAL KISS, FERENC SPERBER, SANDOR GARACZY, ATTILA NEMETH, DEZSO KORBONITS, ERZSEBET MOLNAR, GYORGY MIHALOVICS, LASZLO LEDNICZKY, ISTVAN BONE, KAROLY GYURE, CSABA GONCZI, ERZSEBET SZABO
• Format: Patent
• Language: English
• Published: 07.12.1995
• Edition: 5
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES

The invention relates to 5-(2-chloro-C2-5-alkyl)-4-methyl-1,3-thiazoles of the general formula I, wherein R is a straight-chain 2-chloro-C2-5-alkyl group and a process for their preparation, which is characterized by (A1) reacting a 3-(2-chloro-C2-5-alkyl)-3-thiocyanato-2-propanone of the general formula IV in an organic solvent with gaseous hydrogen chloride to obtain the corresponding 2-chloro-5-(2-chloro-C2-5-alkyl)-4-methyl-1,3-thiazole of the general formula II or (A2) reacting a 3-(2-chloro-C2-5-alkyl)-3-thiocyanato-2-propanone of the above formula IV with an aqueous mineral acid to obtain the corresponding 5-(2-chloro-C2-5-alkyl)-2-hydroxy-4-methyl-1,3-thiazole of the general formula III and reacting the thus obtained compound of the formula III with a halogenating agent to obtain the corresponding 2-chloro-5-(2-chloro-C2-5-alkyl)-4-methyl-1,3-thiazole of the above formula II, and (B) hydrogenating the compound of the general formula II to obtain the 5-(2-chloro-C2-5-alkyl)-4-methyl-1,3-thiazole of the above general formula I. The invention further relates to intermediates for the above process, and pharmaceutical compositions comprising the compounds of formula I.