Hydroxylamine, O-((4-chlorophenyl)methyl)-, hydrochloride (1:1) → N-{4-chloro-2-[1-(4-chlorobenzyloxyimino)propyl]phenyl}trifluoromethanesulfonamide

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Reaction Steps

A solution of N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide 22 (1.75 g, 5.54 mmol), O-(4-chlorobenzyl)hydroxylamine hydrochloride (1.13 g, 5.82 mmol) and anhydrous NaOAc (477 mg, 5.82 mmol) in EtOH (80 mL) was stirred for 15 h at RT. The reaction mixture was concentrated under vacuum and the residue filtered through a pad of silica (eluting with CH2Cl2/PE, 3:2). Purification by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9) afforded a pale yellow solid which was recrystallized from CH2Cl2/PE to give N-{4-chloro-2-[1-(4-chlorobenzyloxyimino)propyl]phenyl}trifluoromethanesulfonamide 11 (1.74 mg, 69%), as a white solid. M.p. 54-55° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.55, br s, 1H, 7.63, d, J=8.8 Hz, 1H, 7.47, d, J=2.2 Hz, 1H, 7.39-7.29, m, 5H; 5.17, s, 2H, 2.84, q, J=7.6 Hz, 2H, 1.18, t, J=7.6 Hz, 3H.

Provenance & Evidence