HCID 10564674, compound → HCID 46840871, compound

Participants

Reaction Steps

To a solution of 2-amino-N-(4-trifluoromethyl-phenyl)-benzamide (0.19 g, 0.68 mmol) and 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (0.16 g, 0.81 mmol) in anhydrous ethanol (15 mL) was added anhydrous copper (II) chloride (0.273 g, 2.03 mmol). The reaction mixture was stirred at reflux for 16 hours under nitrogen and then cooled to room temperature. Ethanol was evaporated under reduced pressure. The residue was taken in ethyl acetate (100 mL). The organic phase was washed with water (2×75 mL), then brine (75 mL), and dried over anhydrous Na2SO4. Solvent was evaporated; crude compound was purified by column chromatography (silica gel 230-400 mesh; 2:3:5 ethyl acetate, hexanes and CH2Cl2 as eluent) to give the title compound as a white solid. Yield: 0.17 g (55%). MP 160-161° C. 1H-NMR (400 MHz, CDCl3): δ 8.34 (d, J=8.00 Hz, 1H), 7.84-7.82 (m, 2H), 7.62-7.53 (m, 3H), 7.31 (d, J=8.40 Hz, 2H), 6.97 (s, 2H), 3.93-3.89 (m, 2H), 3.80 (t, J=5.20 Hz, 2H), 2.15 (s, 6H), 2.07 (t, J=6.40 Hz, 1H).

Provenance & Evidence