反应详情

A solution of N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide 22 (386 mg, 1.22 mmol), O-(4-fluorophenyl)hydroxylamine hydrochloride (200 mg, 1.22 mmol) and anhydrous NaOAc (110 mg, 1.34 mmol) in EtOH (18 mL) was stirred for 15 hours at RT. The reaction mixture was concentrated under vacuum and the residue filtered through a pad of silica (eluting with CH2Cl2/PE, 3:2). The residue was purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:4) to afford N-{4-chloro-2-[1-(4-fluorophenoxyimino)propyl]phenyl}trifluoromethanesulfonamide 130 (420 mg, 81%), as a pale yellow solid. M.p. 47-48° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.25, br s, 1H; 7.71, d, J=8.8 Hz, 1H; 7.58, d, J=2.4 Hz, 1H; 7.40, dd, J=2.4 and 8.8 Hz, 1H; 7.18-7.02, m, 4H; 3.02, q, J=7.6 Hz, 2H; 1.31, t, J=7.6 Hz, 3H.

1. concentrationThe reaction mixture was concentrated under vacuum
2. filtrationthe residue filtered through a pad of silica (eluting with CH2Cl2/PE, 3:2)
3. customThe residue was purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:4)