Dimethylformamide → 2-(3-iodophenyl)-N-(2-methoxyethyl)acetamide

Participants

Reaction Steps

To a solution of 3 iodophenylacetic acid (1.12 g, 4.3 mmol) in dichloromethane (50 mL) was added oxalyl chloride (0.75 mL, 8.6 mmol) and DMF (0.05 mL). The mixture was stirred for 1 h at room temperature and concentrated. The residue was dissolved in dry THF (40 mL) and 2-methoxyethylamine (2.0 mL, 23 mmol) was added. The mixture was stirred for 2 h and concentrated. The residue was partitioned between water and ethyl acetate, the organic phase was collected, washed with 1M HCl, water, saturated NaHCO3, brine, dried (MgSO4), filtered and concentrated to afford pure 151 (1.23 g, 89%). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.64-7.61 (m, 2H), 7.26-7.24 (m, 1H), 7.10-7.06 (m, 1H), 5.81 (br s, 1H), 3.49 (s, 2H), 3.44-3.40 (m, 4H), 3.32 (s, 1H). MS (m/z): 320.1 (M+H).

Provenance & Evidence