Sodium Chloride → 1-Benzyl-alpha,alpha-bis(p-chlorophenyl)imidazole-2-methanol

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Reaction Steps

A solution of 17.4 g (0.11 mol) of N-benzylimidazole in 40 ml. of anhydrous tetrahydrofuran was added dropwise in the course of one hour, at -20° to -30° C. and under a nitrogen atmosphere, to a phenyl lithium solution, prepared from 1.67 g (0.24 gr. at.) of lithium and 18.8 g (0.12 mol) of bromobenzene in 80 ml. of anhydrous diethyl ether. The mixture was heated for about one hour until a brightly red, homogenous solution was obtained. Subsequently a solution of 25.1 g (0.1 mol) of 4,4'-dichlorobenzophenone in 60 ml. of anhydrous tetrahydrofuran was added in the course of one hour at a temperature between -25° and -15° C. The reaction mixture was stirred for 15 hours at room temperature, under the nitrogen atmosphere and it was then poured on 200 g of ice. The aqueous phase was saturated with sodium chloride and the organic phase was separated off and concentrated. The residue was dissolved in a small amount of acetone and the solution was acidified with 2 N hydrochloric acid. Then some toluene was added and the precipitate formed was filtered off. The product was thrice crystallised from a mixture of isopropyl alcohol and petroleum ether (boiling range 28°-40° C.). 1-Benzyl-α,α-bis(p-chlorophenyl)imidazole-2-methanol was obtained. Melting point 167°-168° C.

Provenance & Evidence