3,4-Dichlorobenzyl chloride → HCID 53817886, compound

Participants

Reaction Conditions

Reaction Steps

A 56% dispersion of sodium hydride in mineral oil (240 mg.) is added under nitrogen to a solution of 1.43 g. of 1-[3'-(3",4"-dichlorophenoxy)-2'-hydroxypropyl]imidazole in 4 ml. of dry hexamethylphosphoramide. The reaction mixture is then stirred for 1 hour at 25° C., and then 1 hour at 45° C. The solution is then cooled in an ice bath and 1.07 g. of α,3,4-trichlorotoluene in 1 ml. hexamethylphosphoramide is added dropwise with stirring. The reaction mixture is then stirred for 1 hour at 5° C., and then for 1 hour at 25° C., and finally for 2 hours at 45° C. The mixture is then poured into 100 ml. of water and the resultant aqueous mixture extracted with ether and the ether extracts washed with water. The organic phase is dried over magnesium sulfate and evaporated. The resulting residue is chromatographed on silica gel and eluted with 30% acetone in dichloromethane to yield pure 1-[2'-(3",4"-dichlorobenzyloxy)-3'-(3",4"-dichlorophenoxy)propyl]imidazole which is taken up in ether and treated with nitric acid yielding, after recrystallization of the crude salt from ethyl acetate/ether, 1-[2'-(3",4"-dichlorobenzyloxy)-3'-(3",4"-dichlorophenoxy)propyl]imidazole nitrate, m.p. 116°-118.5° C.

Provenance & Evidence