Chlormidazole

Originator

Diamyceline,Diamant

Definition

ChEBI: Chlormidazole is a member of benzimidazoles.

Manufacturing Process

The first method synthesis of 1-p-chlorobenzyl-2-methylbenzimidazole: 26.4 g of 2-methylbenzimidazole are dissolved in 350 ml of dioxane, 10 g of sodium amide are added there to. After about 5 min 41,2 g of pchlorobenzylbromide are added to the resulting mixture which is then boiled under reflux for 6 hours. Dioxane is removed by distillation. The residue is triturated with dilute hydrochloric acid. The resulting crystalline mass representing the crude hydrochloride of 1-p-chlorobenzyl-2- methylbenzimidazole is filtered off by suction and recrystallized from water. On cooling, colorless crystals are obtained which are dissolved in hot water. Dilute ammonia solution is added to the resulting aqueous solution to render it weakly alkaline. The base of 1-p-chloro-benzyl-2-methylbenzimidazole precipitates, first in liquid form, and gradually solidifies to a white mass of its hydrate. After recyrstallization from aqueous ethanol, the product has a melting point of 67-68°C. The base of 1-p-chlorobenzyl-2- methylbenzimidazole distills in the form of a colorless oil at 240-242°C/12 mm. Its hydrate of the melting point 67-68°C is obtained by trituration with water.
The second method of synthesis of 1-p-chlorobenzyl-2-methylbenzimidazole:
23.3 g of p-chlorobenzyl-o-phenylenediamine are boiled under reflux with 75 ml of glacial acetic acid for 3 hours. Most of the acetic acid is then removed by distillation. Dilute sodium hydroxide solution is added to the residue to render it weakly alkaline. The resulting base of 1-p-chlorobenzyl-2- methylbenzunidazole is purified as such by recrystallization from aqueous ethanol. It may also be converted into its hydrochloride which is then worked up as described hereinabove in the first method of synthesis.

Therapeutic Function

Antifungal