2-Methylimidazole → 1-(4-Imidazolylsulfonyl)-2-methylimidazole

Participants

Reaction Steps

A dry round bottom flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was charged with a filtered solution of 8.33 g of imidazole-4-sulfonylchloride in 300 ml of THF. The clear solution was treated with 8.45 g of 2-methylimidazole in one portion and allowed to stir overnight at room temperature. The reaction mixture was concentrated at reduced pressure to an oily residue. The residue was dissolved in 250 ml water, sodium chloride was added and the solution extracted with five 100 ml portions of ethyl acetate. The extracts were combined, washed with brine, dried (Na2SO4) and concentrated on a rotary evaporator to give 10.0 g of ivory colored product. Recrystallization from ethyl acetate-hexane have 5.57 g in two crops of 1-(4-imidazolylsulfonyl)-2-methylimidazole with mp 158°-9°, λmaxnujol 3.22 (NH), 7.30 (SO2N) and 8.48 μ (SO2N). NMR (DMSO, d6) 520-650 Hz, m, 1H; 499 Hz, d J ~ 1 Hz, 1H; 481 Hz, d, J ~ 1 Hz, 1H (AB pattern); 450 H, d, J = 1 Hz, 1H; 425 Hz, d, J = 1 Hz, 1H (AB pattern); 154 Hz, s, 3H.

Provenance & Evidence