Phosphorus oxychloride → HCID 52025964, compound

Participants

Reaction Steps

To a solution of N-(2-aminophenyl)-2-benzamidoisonicotinamide (0.18 g, 0.53 mmol) in toluene (10 mL) was added phosphorus oxychloride (0.14 mL, 1.57 mmol) at ambient temperature. The resulting solution was refluxed for 5 hours, cooled to ambient temperature and concentrated in vacuo. The residue was taken up in 1 M aqueous sodium hydroxide solution (50 mL) and extracted with dichloromethane (2×50 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography eluting with 20-100% ethyl acetate in hexanes to give N-(4-(1H-benzo[d]imidazol-2-yl)pyridin-2-yl)benzamide as a pale yellow solid (0.02 g, 9%): mp 145-146° C.; 1H NMR (300 MHz, DMSO-d6) δ 11.03 (s, 1H), 9.01 (s, 1H), 8.59 (d, J=5.2 Hz, 1H), 8.12-8.07 (m, 2H), 7.91 (dd, J=5.2, 1.4 Hz, 1H), 7.69 (dd, J=6.0, 3.2 Hz, 2H), 7.66-7.51 (m, 4H), 7.30 (dd, J=6.0, 3.2 Hz, 2H); MS (ES+) m/z 315.5 (M+1).

Provenance & Evidence