1,2-Dichloroethane → HCID 66616681, compound

Participants

Reaction Steps

To a solution of 3-(phenethylthiomethyl)benzoic acid (0.5 g, 1.84 mmol) in DMF (8 mL) were added EDC (0.49 g, 2.57 mmol), HOBT (0.28 g, 1.84 mmol) and 4-fluorophenethylamine (0.24 mL, 1.84 mmol). The clear reaction mixture was stirred at rt for 2 h and diluted with ethyl acetate and 1 N aqueous HCl solution. The organic layer was separated, washed with brine and dried over MgSO4. The filtrate was concentrated in vacuo. The residue was dissolved in DCM and purified by flash chromatography on silica gel eluting with 20% ethyl acetate in dichloromethane to give the desired product (0.34 g, 47%) as a white solid. 1H NMR (CDCl3) δ 7.61 (s, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.41 (d, J=8.0 Hz, 1H), 7.35 (t, J=8.0 Hz, 1H), 7.24 (d, J=8.0 Hz, 2H), 7.20-7.11 (m, 5H), 6.97 (t, J=8.0 Hz, 2H), 6.11 (s, 1H), 3.69 (s, 2H), 3.67-3.63 (m, 2H), 2.94-2.79 (m, 4H), 2.63-2.61 (m, 2H). MS (ESI): 394.1 (M+H)+.

Provenance & Evidence