N-Methylacetamide → 1,2-Dimethylbenzimidazole

Participants

Reaction Steps

Method A applied to 1-iodo-2-nitrobenzene (125 mg, 0.5 mmol) and N-methylacetamide (44 mg, 0.6 mmol) yielded the title compound as pale yellow solid (62 mg, 85%). mp 101° C. to 103° C. 1H NMR (DMSO) δ 2.79 (s, 3H), 3.92 (s, 3H), 7.46-7.55 (m, 2H), 7.78 (d, J=7.4Hz, 1H), 7.89 (d, J=7.1Hz, 1H); 13C NMR δ 11.6, 30.8, 112.3, 114.1, 124.9, 125.3, 132.6, 151.9, 158.3. HRMS (FAB): cal. for C9H11N2 [M+H+]: 147.0922; found: 147.0917. Method C afforded 38 mg of the title compound (52% yield).

Provenance & Evidence