Water → 2-Methyl-1-(4-nitrobenzyl)-1H-imidazole

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Reaction Steps

Sodium hydride (2.45 g, 61.0 mmol, 60% dispersion in oil) was added to a solution of 2-methylimidazole (5.0 g, 60.9 mmol) in DMF (100 ml). The mixture was stirred at room temperature for 0.25h before adding 4-nitrobenzyl bromide (13.2 g, 61.0 mmol) and heating at 110° C. for 2h followed by stirring at room temperture for 16h. Water (200 ml) and ethyl acetate (500 ml) were added, the aqueous separated and extracted with ethyl acetate (2×500 ml). The combined extracts were washed with water (3×250 ml), dried (MgSO4) and evaporated. The crude product was chromatographed on silica-gel eluting with CH2Cl2 /MeOH (96:4) to give the title-product (1.58 g); δ (360 MHz, CDCl3) 2.34 (3H, s, CH3), 5.16 (2H, s, CH2), 6.67 (1H, d, J=1.3 Hz, Ar--H), 7.03 (1H, d, J=1.3 Hz, Ar--H), 7.19 (2H, d, J=9.5Hz, Ar--H), 8.22 (2H, d, J=9.5Hz, Ar--H).

Provenance & Evidence