Sodium Acetate → N-{4-chloro-2-[1-(4-chlorophenoxyimino)butyl]phenyl}trifluoromethanesulfonamide

Participants

Reaction Steps

A solution of N-[4-chloro-2-(2,2-dimethylpropionyl)phenyl]trifluoromethanesulfonamide 29C (300 mg, 0.87 mmol), O-(4-chlorophenyl)hydroxylamine hydrochloride (173 mg, 0.96 mmol) and anhydrous NaOAc (80 mg, 0.96 mmol) in EtOH (20 mL) was stirred for 40 hours at RT. The reaction mixture was concentrated under vacuum, the residue filtered through a pad of silica (eluting with CH2Cl2/PE, 3:7) and the solvent removed under reduced pressure. The residue was purified by recrystallization from CH2Cl2/PE to afford N-{4-chloro-2-[1-(4-chlorophenoxyimino)butyl]phenyl}trifluoromethanesulfonamide 182 (40 mg, 10%), as a yellow solid. M.p. 69-70° C. 1H n.m.r. (200 MHz, CDCl3) δ 7.52, d, J=8.8 Hz, 1H; 7.43, dd, J=2.2 and 8.8 Hz, 1H; 7.25, d, J=9.2 Hz, 2H; 7.18, d, J=2.2 Hz, 1H; 7.01, d, J=9.2 Hz, 2H; 6.43, br s, 1H; 1.33, s, 9H.

Provenance & Evidence