Chloroacetyl chloride → HCID 53477038, compound

Participants

Reaction Steps

N-(4-(trifluoromethyl)benzyl)-2-amino-3-hydroxybenzamide 22a (1 g, 3.2 mmol) was dissolved in 20 ml of DMF and at 0° C. TEA (0.9 ml, 2 equiv.) and chloroacetyl chloride (0.3 ml, 1.2 equiv.) were added. The mixture was stirred at rt for 2 hours. K2CO3 (885 mg, 2 equiv.) was added and the reaction was stirred at rt for 20 hours. The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column using AcOEt 1/petroleum ether 1 as eluant gave 500 mg of a white solid. Yield=44% 1HNMR (DMSO, 200 MHz) δ 4.56 (2H, d, J=5.4 Hz), 4.65 (2H, s), 7.04 (2H, t), 7.17 (1H, d, J=7.8 Hz), 7.55 (2H, d, J=8 Hz), 7.71 (2H, d, J=8.2 Hz), 9.52 (1H, bs), 10.96 (1H, bs); [M+1] 351.1 (C17H13F3N2O3 requires 350.3).

Provenance & Evidence