Imidazole → (E)-4-(1H-Imidazol-1-yl)butoxystilbene hydrochloride

Participants

Reaction Steps

A solution of the (E)-4-chlorobutoxystilbene (2.0 g, 7.0 mmol) and imidazole (1.0 g, 14 mmol) in 20 mL of 2-methoxyethyl ether was heated to 120° C. for 24 hours. The solvent was removed by distillation and the resulting residue was chromatographed (flash, SiGel, 9:1 CH2Cl2 -MeOH). The hydrochloride salt was made in HCl/MeOH and recrystallized from acetone to give 2.7 g (95%) of the title compound as an off-white solid. m.p. 208°-210° C. IR(KBr): 3400,1590cm-1. MS: 319(MH)+. 1H NMR(CD3OD): δ9.21(s,1H), 7.65-6.82(m,13H), 4.35(t,2H), 4.02 (t,2H), 2.01(m,4H).

Provenance & Evidence