Water → 4-Iodo-2-methyl-1-(3-methyl-4-nitrophenyl)-1H-imidazole

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Reaction Steps

A mixture of 5-fluoro-2-nitrotoluene (7.9 g), 4-iodo-2-methylimidazole (9.0 g) and sodium carbonate (4.5 g) was heated with stirring in dimethylformamide (50 cm3) at 120° for 16 hours under nitrogen. The mixture was poured into water (50 cm3) and extracted with chloroform (3×100 cm3). The combined and dried (MgSO4) organic extracts were concentrated in vacuo to give a solid which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with ethyl acetate:toluene, 1:5 by volume. Combination and evaporation of appropriate fractions afforded a solid which was recrystallised from dichloromethane-hexane to give the title compound, m.p. 146°-8°, (4.0 g).

Provenance & Evidence