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Clemizole

Clemizole Structure
Clemizole
  • CAS No.442-52-4
  • Chemical Name:Clemizole
  • CBNumber:CB3875322
  • Molecular Formula:C19H20ClN3
  • Formula Weight:325.84
  • MOL File:442-52-4.mol
Clemizole Property
  • Melting point: :239-241℃
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal word
  • Hazard statements
  • Precautionary statements

Clemizole Chemical Properties,Usage,Production

  • Originator Allercur,Roerig,US,1960
  • Definition ChEBI: 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 Process From 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 Function Antihistaminic
Clemizole Preparation Products And Raw materials
Raw materials
Preparation Products
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442-52-4, ClemizoleRelated Search:
  • Clemizole (free base)
  • 1-[(4-chlorophenyl)methyl]-2-(1-pyrrolidinylmethyl)-1H-benzimidazole (Clemizole)
  • 1-(4-Chlorobenzyl)-2-(pyrrolizinomethyl)-1H-benzimidazole
  • 1-(p-Chlorobenzyl)-2-(1-pyrrolidinylmethyl)-1H-benzimidazole
  • Histacur
  • 1-(4-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)benzimidazole
  • 1-[(4-chlorophenyl)methyl]-2-(pyrrolidin-1-ylmethyl)benzimidazole
  • 1-[(4-chlorophenyl)methyl]-2-(1-pyrrolidinylmethyl)-1H-benzimidazole
  • 1-(4-CHLOROBENZYL)-2-(PYRROLIDIN-1-YLMETHYL)-1H-BENZO[D]IMIDAZOLE HYDROCHLORIDE
  • 1-p-Chlorobenzyl-2-pyrrolidino-methylbenzimidazole
  • Depocural
  • Histakool
  • Lergopenin
  • NSC 46261
  • 1-p-Chlorobenzyl-2-[1-pyrrolidinylmethyl] benzimidazole
  • 1-(p-Chlorobenzyl)-2-pyrrolidylmethylenebenzimidazole
  • 1H-Benzimidazole,1-[(4-chlorophenyl)methyl]-2-(1-pyrrolidinylmethyl)-
  • 1-(4-Chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzo[d]imidazole
  • Clemizole USP/EP/BP
  • 442-52-4
  • C19H20ClN3
  • Inhibitors
  • API intermediates