Ethyl 11-bromoundecanoate → HCID 23220722, compound

Participants

Reaction Steps

To a solution of 12.6 g (0.05 mole) 4,5-diphenyl-2-imidazolethiol in 125 ml dimethylformamide was added, dropwise, 14.2 g (0.05 mole) ethyl-11-bromoundecanoate in 40 ml dimethylformamide and the reaction mixture was stirred at reflux under nitrogen overnight. The cooled solution was poured into 5% sodium bicarbonate and ice and then extracted with ethyl acetate. The organic layer was backwashed with 5% sodium bicarbonate, water, and saturated sodium chloride solution, then dried over magnesium sulfate and the solvent was removed under vacuum. The residue was chromatographed using hexane:ethyl acetate (9:1). The resulting solid was triturated with hexane to give 13.58 g (0.029 mole) of the title compound as a white solid, mp=57°-59° C. 1HNMR(DMSO-d6): δ12.6(s,1H), 7.6-7.1(m,10H), 4.0(q,2H,J=8Hz), 3.5(t,2H,J=7Hz), 2.25(t,2H,J=7Hz), 1.8-1.1(m.21H).

Provenance & Evidence