Acetic Acid → N-[4-chloro-2-(1-ethoxyiminobutyl)phenyl]trifluoromethanesulfonamide

Participants

Reaction Steps

N,N-Dimethylethylenediamine (254 μL, 2.20 mmol) was added to a solution of N-ethoxyphthalimide (287 mg, 1.50 mmol) in EtOH (5 mL), and the reaction allowed to stir at RT for 15 hours. Glacial acetic acid (2 mL) was then added to adjust the mixture to ca. pH 4, followed by the addition of N-(2-butyryl-4-chlorophenyl)trifluoromethanesulfonamide 29A (330 mg, 1.0 mmol), and the reaction stirred for 15 hours at RT. The reaction mixture was concentrated under vacuum, and the residue dissolved in Et2O (50 mL) and washed with water, brine, dried over MgSO4 and the solvent removed under reduced pressure. The residue was filtered through a pad of silica (eluting with CH2Cl2/PE, 1:1), the solvent evaporated under reduced pressure and the residue purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:19) to afford N-[4-chloro-2-(1-ethoxyiminobutyl)phenyl]trifluoromethanesulfonamide 193 (82 mg, 22%), as a colorless oil. 1H n.m.r. (400 MHz, CDCl3) δ 12.10, br s, 1H; 7.67, d, J=8.8 Hz, 1H, 7.47, d, J=2.4 Hz, 1H, 7.32, dd, J=2.4 and 8.8 Hz, 1H, 4.27, q, J=7.2 Hz, 2H, 2.78, m, 2H, 1.59, sextet, 2H; 1.37, t, J=7.2 Hz, 3H, 1.02, t, J=7.6 Hz, 3H. HRMS (M+) 372.0514.

Provenance & Evidence