Sodium hydride → HCID 66748876, compound

Participants

Reaction Steps

A solution of N-(2-fluoro-4-iodophenyl)-N′-methylurea (6-2, 2.9 g, 9.86 mmol) in DMF (12 ml) were treated with Sodium Hydride (308 mg, 12.8 mmol, 1.3 eq). The reaction mixture was irradiated in a microwave at 200 deg C. for 10 min. The starting material was consumed, so it was partitioned between EtOAc (2×75 ml) and water (85 ml), and the combined organic layers were dried over Na2SO4 and concentrated. The residual crude maroon oil was purified via flash column chromatography (SiO2: 100% Hex to 50:50 Hex/EtOAc), which afforded the title compound, 6-iodo-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (6-3), as a tan solid. 1H NMR (500 MHz, CDCl3) δ 9.64 (bs, 1H), 7.39 (d, 1H, J=6.6 Hz), 7.30 (s, 1H), 6.87 (d, 1H, J=8.1 Hz), 3.39 (s, 3H). LRMS m/z: Calc'd for C8H7IN2O (M+H) 275.1, found 274.9.

Provenance & Evidence