Acetanilide → 5-Methoxy-2-methyl-1-phenyl-1H-benzimidazole

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Reaction Steps

Method A applied to 4-chloro-3-nitroanisol (84 mg, 0.5 mmol) and N-phenylacetamide (81 mg, 0.6 mmol) yielded the title compound as a pale yellow solid. mp 88-90° C. 1H NMR (DMSO) δ 2.61 (s, 3H), 3.88 (s, 3H), 7.07 (d, J=8.9Hz, 1H), 7.25 (d, J=8.9 Hz, 1H), 7.38 (br s, 1H), 7.65-7.73 (m, 5H); 13C NMR δ 12.5, 55.9, 97.7, 112.6, 114.7, 126.9, 127.8, 130.2, 130.3, 132.8, 133.1, 151.2, 157.6, 157.8. HRMS (FAB): cal. for C15H15N2O [M+H+]: 239.1184; found: 239.1180.

Provenance & Evidence