Oxalic Acid → (E)-5-Methyl-1-(2-pyridyl)-2-[2-(2-thienyl)ethenyl]-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-(2-thienyl)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/n-hexane yielded the titled compound. MW: 417.42; mp: 181.5-182.0° C.; 1H-NMR (DMSO) δ: 8.78-8.72 (1H, m), 8.16 (1H, t, J=7.7 Hz), 8.00 (1H, d, J=15.8 Hz), 7.69 (1H, d, J=8.1 Hz), 7.62-7.50 (3H, m), 7.39 (1H, br.s), 7.31 (1H, d, J=8.1 Hz), 7.15-7.05 (2H, m), 6.86 (1H, d, J=15.8 Hz), 2.42 (3H, s).

Provenance & Evidence