PRODUCTION OF IMIDAZOLE DERIVATIVE

PURPOSE:To obtain the titled compound useful as an intermediate for cimetidine at a low cost, by reacting 4-methyl-5-hydroxymethylimidazole with S,S'-bis(2- aminoethyl)dithiocarbonate as raw materials in acidic solvent. CONSTITUTION:Readily synthesized 4-methyl-5-hydroxymethylimidazole is react...

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Bibliographic Details
Main Authors FUJII KENICHI, KAWASAKI NOBORU, NOGUCHI YOSHIAKI
Format Patent
LanguageEnglish
Published 28.02.1989
Subjects
CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
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Summary:PURPOSE:To obtain the titled compound useful as an intermediate for cimetidine at a low cost, by reacting 4-methyl-5-hydroxymethylimidazole with S,S'-bis(2- aminoethyl)dithiocarbonate as raw materials in acidic solvent. CONSTITUTION:Readily synthesized 4-methyl-5-hydroxymethylimidazole is reacted with S,S'-bis(2-aminoethyl)dithiocarbonate expressed by formula II which can be readily synthesized by reacting 2-mercaptothiazoline and chloroethylamine in an acidic solvent, such as hydrochloric acid or acetic acid, in >=5wt.% concentration at 70 deg.C - refluxing temperature for 5-30hr to vacuum concentrate the resultant reaction solution and separate the aimed compound, such as 4- methyl-5-[(2-aminoethyl)-thiomethyl]-imidazole hydrochloride, expressed by formula III and useful as a synthetic intermediate for cimetidine which is an antiulcer agent having inhibitory action on histamine H2 receptor, etc., as a solid substance. The resultant substance is then recrystallized from a alcohols to afford the aimed compound.
Bibliography:Application Number: JP19870209381