Hydrochloric Acid → N-(8-phenyl-octyl)-3,5-bis(m-trifluoromethylphenyl)4hydroxy-benzamide

Participants

Reaction Steps

To 3,5-bis-(m-trifluoromethylphenyl)-4-hydroxy-benzoic acid ethyl ester (0.315 g, 0.74 mmol, 1 eq) was added thionyl chloride (2 mL) and the reaction was stirred overnight at rt and concentrated in vacuo. It was then added to a solution of phenyl octyl amine (0.222 mL, 1.12 mmol, 1 .51 eq) and triethylamine (0.470 mL, 3.37 mmol, 4.6 eq). The reaction was stirred at rt 1 h, poured into 0.1 N HCl solution and extracted with Et2O. The combined organics were washed with 1N HCl (×3), dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (20% EtOAc:hexane) to afford title compound (0.393 g, 86%) as a colorless oil. 1H NMR (DMSO-d6) δ9.30 (s, 1H); 8.42 (t, 1H); 7.91-7.85 (m, 4H); 7.82 (s, 2H); 7.75-7.65 (m, 4H); 7.26-7.10 (m, 5H); 3.23 (dd, 2H); 2.52 (t, 2H); 1.52 (m, 4H); 1.27 (m, 8H); IR (film) 3330, 2980, 2840, 1640, 1600, 1550, 1470, 1320, 1180, 1120, 1080, 900, 805 cm−1; mass spectrum [(+)APCI], m/z 614 (M+H)+; Anal. Calcd. for C35H33F6NO2: C, 68.51; H, 5.42; N, 2.28, Found: C, 66.76; H, 5.46; N, 2.18.

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