Dichloroacetyl chloride → HCID 46916410, compound

Participants

Reaction Steps

To a solution of (3-quinoxalin-2-ylphenyl)amine (128 mg, 0.578 mmol) and DIEA (115 μL, 0.694 mmol) in THF (5 mL), dichloroacetyl chloride (61 μL, 0.636 mmol) was added at room temperature. The reaction mixture was stirred at room temperature for 48 hrs, diluted with ethyl acetate (20 mL). The organic phase was washed with water (10 mL) and then brine (10 mL), dried over MgSO4, and the solvent was evaporated in vacuo to afford a light-yellow solid. The solid was triturated with Et2O, filtered, and submitted to preparative LCMS to afford 3-chloro-N-[3-(quinoxalin-2-yl)phenyl]propanamide (50 mg, 28% yield). LCMS calculated for C17H14ClN3O (M+H): 312.08. found 312.14. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.30 (1H, br. s), 9.50 (1H, s), 8.52 (1H, m), 6.65-8.60 (2H, m), 8.58 (1H, d, J=7 Hz), 7.95-7.84 (3H, m), 7.55 (1H, m), 3.91 (2H, t, J=7.1 Hz), 2.88 (2H, t, J=7.1 Hz).

Provenance & Evidence