Oxalic Acid → (E)-5-Methoxy-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-methoxy-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: 423.45; mp: 180.0-181.0° C.; 1H-NMR (DMSO) δ: 8.76 (1H, d, J=4.0 Hz), 8.18 (1H, td, J=7.3, 1.8 Hz), 7.99 (1H, d, J=15.8 Hz), 7.72 (1H, d, J=7.7 Hz), 7.65-7.56 (2H, m), 7.42 (1H, d, J=3.7 Hz), 7.34 (1H, d, J=8.8 Hz), 7.24 (1H, d, J=2.2 Hz), 7.14-7.09 (1H, m), 6.92-6.84 (2H, m), 3.83 (3H, s).

Provenance & Evidence