Dimethylformamide → 3-Iodobenzamide

Participants

Reaction Steps

3-Iodo-benzamide was prepared using a modification of the procedure by Remsen. (Remsen; Reid Am. Chem. J. 1899, 21, 289.) 3-Iodo-benzoic acid (28.68 g, 116 mmol) was stirred in CH2Cl2 (200 mL) at 23° C. under argon. Oxalyl chloride (30.2 mL, 349 mmol) was added slowly, and slow gas evolution was observed. DMF (0.1 mL) was then added, accelerated gas evolution considerably, and the reaction was stirred for. 2 h. Solvent was removed, and the brown oily residue was dissolved in THF (50 mL) and added to a solution of 18% aqueous NH4OH (260 mL) at 0° C. After stirring the mixture for 15 min, the liquid was decanted off, and the remaining sludge was acidified with 1 N HCl. The white solid was collected by filtration, washed with water, and dried under vacuum to give 25.68 g (90%) of 3-iodo-benzamide compound 32. 1H NMR (DMSO-d6) δ 8.21 (1 H, t, J=1.5 Hz), 8.05 (1 H, s), 7.87 (2 H, dd, J=8.1, 1.5 Hz), 7.47 (1 H, s), 7.25 (1 H, t, J=7.8 Hz); IR (KBr) 3343, 3164, 1661, 1628, 1561, 1424, 1389, 1125. Anal. (C7H6INO) C, H, N.

Provenance & Evidence