PROCESS FOR THE PREPARTION OF 4-METHYL-5-(2-CHLOROETHYL)-THIAZOLE AND ANALOGUES THEREOF

• Main Authors: MOLNAR ERZSEBET, MICHALOVICS GYORGY, GONCZI CSABA, SUTO MIHALY, SPERBER FERENC, BAN KAROLY, MORASZ FERENC, GARACZY SANDOR, PALOSI ENDRE, KORBONITS, KISS PAL, SZABO ERZSEBET, NEMETH ATTILA, GYURE KAROLY, BUTTKAI ILDIKO, SZALAY ERZSEBET, GYORI PETER, HEJA GERGELY, HUSZAR CSABA, LEDNICZKY LASZLO, SZVOBODA IDA, KOVARI ARPAD, BONE ISTVAN
• Format: Patent
• Language: English
• Published: 08.02.1995
• Edition: 6
• 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.