(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole → (E)-5-Methoxy-2-[2-(2-methyl-3-furyl)ethenyl]-1-(2-pyridyl)-1H-benzimidazole

Participants

Reaction Steps

(E)-3-(2-Methyl-3-furyl)acrylic acid (0.30 g, 2 mmol) was dissolved into thionyl chloride (5 ml) and the mixture was heated to reflux for 80 min. Volatiles were removed by evaporation to give crude (E)-3-(2-methyl-3-furyl)acryloyl chloride. The titled compound was prepared from 2-amino4-methoxy-N-(2-pyridyl)aniline (0.43 g, 2 mmol) and (E)-3-(2-methyl-3-furyl)acryloyl chloride obtained as above according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). Recrystallization from a mixture of isopropyl ether (3 ml) and ethyl acetate (3 ml) to give 0.10 g (16%) of the titled compound. MW: 331.38; mp: 139.0-140.0° C.; 1H-NMR (CDCl3) δ: 8.75 (1H, dd, J=5.8, 2.2 Hz), 7.97 (1H, ddd, J=7.7, 7.7, 2.2 Hz), 7.79 (1H, d, J=15.8 Hz), 7.77-7.40 (2H, m), 7.33 (1H, d, J=8.8 Hz), 7.30 (1H, d, J=1.8 Hz), 7.24 (1H, d, J=2.0 Hz), 6.88 (1H, dd, J=9.2, 2.0 Hz), 6.72 (1H, d, J=15.8 Hz), 6.44 (1H, d, J=1.8 Hz), 3.89 (3H, s). 2.43 (3H, s).

Provenance & Evidence