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

Participants

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 0.25 h before adding 4-nitrobenzyl bromide (13.2 g, 61.0 mmol) and heating at 110° C. for 2 h followed by stirring at room temperature for 16 h. 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 (4%) to give the title-product (1.58 g, 10.5%); δ (360 MHz, CDCl3) 2.34 (3H, s, Me); 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=9.5 Hz, Ar-H); 8.22 (2H, d, J=9.5 Hz, Ar-H).

Provenance & Evidence