4-(Trifluoromethyl)benzoic acid → HCID 67376786, compound

Participants

Reaction Conditions

Reaction Steps

4-(Trifluoromethyl)benzoic acid (0.416 g, 2.187 mmol), (Z)—N-hydroxy-2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetimidamide (0.451 g, 1.458 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.559 g, 2.92 mmol) in dichloroethane were stirred together at room temperature for 3 hours. The reaction was then heated to 85° C. and stirred at this temperature for 16 hours. The reaction was cooled, poured in ethyl acetate/1 N HCl (1:1, 200 mL) and the layers separated. The organic layer was washed with brine (100 mL), dried over magnesium sulfate and concentrated. The residue was loaded onto a GraceResolv™ 12 g silica gel column (Grace Davison Discovery Sciences) and eluted with a gradient of 5% ethyl acetate/hexanes to 35% ethyl acetate/hexanes (flow=40 mL/minute) over 30 minutes to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.20 (d, J=8.3, 2H), 7.80 (d, J=8.4, 2H), 7.48-7.15 (m, 10H), 4.81 (s, 2H), 3.50 (t, J=6.5, 2H), 2.84 (t, J=6.5, 2H); MS (ESI+) m/z 464.1 (M+H)+.

Provenance & Evidence