N-butyl-8-(4,5-diphenyl-1H-imidazol-2-ylthio)octanamide → HCID 19021759, compound

Participants

Reaction Conditions

Reaction Steps

Part B. To a solution of lithium aluminum hydride (0.46 g, 0.012 mol) in dry tetrahydrofuran (15 mL) was added, dropwise, a solution of N-butyl-8-(4,5-diphenyl-1H-imidazol-2-ylthio)octanamide (1.20 g, 0.0027 mol) in tetrahydrofuran (8 mL) and the reaction mixture was stirred at reflux for 18 hours. The reaction mixture was cooled to 0° C. and quenched by the slow and careful sequential addition of water (0.46 mL), 15% sodium hydroxide (1.38 mL), and water (1.38 mL) and then the reaction mixture was stirred at 0° for 30 minutes. The solution was dried over magnesium sulfate and concentrated under vacuum, and the residue was chromatographed with 1:1 hexane-ethyl acetate and then with a gradient of 1:0 to 8:2 to 1:1 ethyl acetate-methanol. The resulting solid was triturated with hexane to give N-butyl-8-(4,5-diphenyl-1H-imidazol-2-ylthio)octanamine (0.45 g, 0.001 mol) as a white solid, mp 75°-78°. 1H NMR (CDCl3) δ7.6-7.1(m,10H), 3.1(t,2H,J=7Hz), 2.5(t,2H,J=7Hz), 1.7-1.0(m,16H), 0.9(t,3H,J=8Hz).

Provenance & Evidence