Carbon Dioxide → N-{[2,4-bis(methyloxy)phenyl]methyl)-2-chloro-5-iodobenzamide

Participants

Reaction Steps

2-Chloro-5-iodobenzoic acid (2 g, 7.08 mmol) in 25 mL THF was treated with 1,1′-carbonyldiimidazole (1.15 g, 7.08 mmol) at ambient temperature until CO2 evolution ceased (˜20 min). 2,4-Dimethoxybenzylamine (1.18 g, 7.08 mmol) was added and stirred at ambient temperature for 16 h. The reaction mixture was concentrated to dryness, partitioned between EtOAc and saturated NaHCO3, the organic phase isolated, dried over MgSO4, filtered and concentrated to give N-{[2,4-bis(methyloxy)phenyl]methyl}-2-chloro-5-iodobenzamide (3.00 g, 6.95 mmol) as a pale yellow oil that crystallized on standing. 1H NMR (300 MHz, CDCl3) d 7.95 (d, J=2.2 Hz, 1H), 7.62 (dd, J=8.5, 2.2 Hz, 1H), 7.25 (m, 1H), 7.10 (m, 1H), 6.63 (m, 1H), 6.45 (m, 2H), 4.55 (d, J=5.7 Hz, 2H), 3.83 (s, 3H), 3.80 (s, 3H). LCMS ES+ 431.82, 433.77 (M+H).

Provenance & Evidence