Oxalic Acid → (E)-2-[2-(3-Furyl)ethenyl]-5-methyl-1-(2-pyridyl)-1H-benzimidazole oxalate

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Reaction Steps

Free base of the titled compound was prepared from 4-methyl-2-amino-N-(2-pyridyl)aniline and (E)-3-(3-furyl)acryloyl chloride according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base and oxalic acid were dissolved into ethyl acetate. Concentration and recrystallization from ethyl acetate-hexane yielded the titled compound. MW: 391.38; mp: 197.0-198.0° C.; 1H-NMR (DMSO) δ: 8.78-8.74 (1H, m), 8.16 (1H, td, J=7.7, 2.2 Hz), 8.05 (1H, br.s), 7.77 (1H, d, J=15.8 Hz), 7.70-7.67 (2H, m), 7.65-7.59 (1H, m), 7.51 (1H, br.s), 7.32 (1H, d, J=8.4 Hz), 7.10-7.06 (1H, m), 6.89 (1H, d, J=15.8 Hz), 6.81 (1H, br.s), 2.44 (3H, s).

Provenance & Evidence