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Clemizole

Basic information Safety Related Supplier
Clemizole Basic information
Clemizole Chemical Properties
  • Melting point:239-241℃
Clemizole Usage And Synthesis
  • OriginatorAllercur,Roerig,US,1960
  • DefinitionChEBI: A member of the class of benzimidazoles that is 1H-benzimidazole substituted by a pyrrolidin-1-ylmethyl and a 4-chlorobenzyl groups at positions 2 and 1 respectively.
  • Manufacturing ProcessFrom 13.1 g of N-p-chlorobenzyl-2-nitroaniline (MP 110°C, obtained in the form of orange-red needles, from o-nitrochlorobenzene and pchlorobenzylamine by reaction for 3 hours at 150°C) by reduction with Raneynickel and hydrogen, in which reaction the substance may be suspended in methanol or dissolved in methanol-ethyl acetate at normal pressure and at about 40°C with combination of the theoretical quantity of hydrogen, 12.2 g are obtained of o-amino-N-p-chlorobenzylaniline, which after recrystallization from aqueous methanol has a MP of 90°C.
    8 g of o-amino-N-p-chlorobenzylaniline and 2.8 g of pyridine are dissolved in dry ether and reacted with an ethereal solution of 3.9 g of chloracetyl chloride with cooling in a mixture of ice and common salt. 8 g of N-p-chlorobenzyl-N'- chloracetyl-o-phenylene diamine are obtained which can be worked up in the form of the crude product and, in the slightly colored form, has a MP of 130°C.
    7.6 g of this compound are boiled with 3.9 g of pyrrolidine in 70 cc of toluene for some hours under reflux. After extraction by shaking with water and treatment with hydrochloric acid the hydrochloride is produced of N-pchlorobenzyl-N'-pyrrolidylacetyl-o-phenylene diamine together with some 1-pchlorobenzyl-2-N-pyrrolidylmethyl-benzimidazole. The former, after recrystallization from butanol, melts with foaming at 205°C, the latter, after recrystallization from butanol melts at 239°C to 241°C, and is in the form of white microscopic rods. Boiling in nitrobenzene converts the former compound into the latter.
  • Therapeutic FunctionAntihistaminic
Clemizole Preparation Products And Raw materials
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