Dicyclohexylcarbodiimide → 2-(2,4-Difluoro-phenyl)-N-[5-(4,5-diphenyl-1H-imidazol-2-ylsulfanyl)-pentyl]-N-heptyl-acetamide

Participants

Reaction Steps

To a solution of N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-1-heptanamine (2.2 g, 0.005 mol), 1-hydroxybenzotriazole hydrate (0.81 g, 0.006 mol), and 2,4-difluorophenylacetic acid (1.12 g, 0. 0065 mol) in N,N-dimethylformamide (50 mL) at 0° was added, portionwise as a solid, dicyclohexylcarbodiimide (1.24 g, 0.006 mol). The reaction mixture was stirred at 0° for 2.5 hours, then at ambient temperature for 72 hours . The solids were filtered and washed with chloroform. The filtrate was concentrated under vacuum and the residue (5.2 g) was chromatographed with 7:3 hexane-ethyl acetate. The resulting solid was triturated with hexane to give the title compound (2.59 g, 0.0044 mol) as a yellow oil. 1H NMR (CDCl3) δ 7.6-7.0(m,11H), 6.8-6.5(m,2H), 3.7(d,2H,J=13.7 Hz), 3.5(t,2H,J=6.4 Hz), 3.4-3.0(m,3 H), 2.9(t,2H,J=6.1 Hz), 1.8-1.1(m,17H), 0 0.9(t,3H,J=6.6 Hz).

Provenance & Evidence