Benzyl Chloride → HCID 20026628, compound

Participants

Reaction Steps

A mixture of 3 parts of 5-(1H-imidazol-1-ylmethyl)-2-phenyl-1H-benzimidazol-1-ol and 47 parts of N,N-dimethylformamide was stirred till a clear solution was obtained. 0.5 Parts of a sodium hydride dispersion 50% were added portionwise and stirring was continued till hydrogen evolution had ceased. Upon complete addition, 1.2 parts of (chloromethyl)benzene were added at once at room temperature. Upon complete reaction, the N,N-dimethylformamide layer was evaporated. The residue was taken up in water and the product was extracted with methylbenzene and a mixture of trichloromethane and methanol (90:10 by volume). The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from ethyl acetate. The product was filtered off, washed with a small amount of ethyl acetate and 2,2'-oxybispropane and dried in vacuo at 50° C., yielding 2.64 parts (66.7%) of 5-(1H-imidazol-1-ylmethyl)-2-phenyl-1-(phenylmethoxy)-1H-benzimidazole; (compound 253).

Provenance & Evidence