O-[(4-bromophenyl)methyl]hydroxylamine;hydrochloride

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of N-(2-benzoyl-4-chlorophenyl)trifluoromethanesulfonamide 25 (370 mg, 1.02 mmol), O-(4-bromobenzyl)hydroxylamine hydrochloride (270 mg, 1.13 mmol) and anhydrous NaOAc (90 mg, 1.10 mmol) in EtOH (20 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). Purification by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9) afforded N-{2-[(4-bromobenzyloxyimino)phenylmethyl]-4-chlorophenyl}trifluoromethanesulfonamide 64 (210 mg, 38%), as a yellow solid. M.p. 55-56° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.32, br s, 1H; 7.66, d, J=9.0 Hz, 1H; 7.55-7.48, m, 5H; 7.33-7.20, m, 5H; 6.88, d, J=2.4 Hz, 1H; 5.11, s, 2H. The reaction mixture was concentrated under vacuum 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)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of N-(2-benzoyl-4-chlorophenyl)trifluoromethanesulfonamide 25 (370 mg, 1.02 mmol), O-(4-bromobenzyl)hydroxylamine hydrochloride (270 mg, 1.13 mmol) and anhydrous NaOAc (90 mg, 1.10 mmol) in EtOH (20 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). Purification by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9) afforded N-{2-[(4-bromobenzyloxyimino)phenylmethyl]-4-chlorophenyl}trifluoromethanesulfonamide 64 (210 mg, 38%), as a yellow solid. M.p. 55-56° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.32, br s, 1H; 7.66, d, J=9.0 Hz, 1H; 7.55-7.48, m, 5H; 7.33-7.20, m, 5H; 6.88, d, J=2.4 Hz, 1H; 5.11, s, 2H. The reaction mixture was concentrated under vacuum 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)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of N-(2-benzoyl-4-chlorophenyl)trifluoromethanesulfonamide 25 (370 mg, 1.02 mmol), O-(4-bromobenzyl)hydroxylamine hydrochloride (270 mg, 1.13 mmol) and anhydrous NaOAc (90 mg, 1.10 mmol) in EtOH (20 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). Purification by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9) afforded N-{2-[(4-bromobenzyloxyimino)phenylmethyl]-4-chlorophenyl}trifluoromethanesulfonamide 64 (210 mg, 38%), as a yellow solid. M.p. 55-56° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.32, br s, 1H, 7.66, d, J=9.0 Hz, 1H, 7.55-7.48, m, 5H, 7.33-7.20, m, 5H, 6.88, d, J=2.4 Hz, 1H, 5.11, s, 2H. The reaction mixture was concentrated under vacuum 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)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of N-(2-benzoyl-4-chlorophenyl)trifluoromethanesulfonamide 25 (370 mg, 1.02 mmol), O-(4-bromobenzyl)hydroxylamine hydrochloride (270 mg, 1.13 mmol) and anhydrous NaOAc (90 mg, 1.10 mmol) in EtOH (20 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). Purification by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9) afforded N-{2-[(4-bromobenzyloxyimino)phenylmethyl]-4-chlorophenyl}trifluoromethanesulfonamide 64 (210 mg, 38%), as a yellow solid. M.p. 55-56° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.32, br s, 1H; 7.66, d, J=9.0 Hz, 1H; 7.55-7.48, m, 5H; 7.33-7.20, m, 5H; 6.88, d, J=2.4 Hz, 1H; 5.11, s, 2H. The reaction mixture was concentrated under vacuum 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)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of N-(2-benzoyl-4-chlorophenyl)trifluoromethanesulfonamide 25 (370 mg, 1.02 mmol), O-(4-bromobenzyl)hydroxylamine hydrochloride (270 mg, 1.13 mmol) and anhydrous NaOAc (90 mg, 1.10 mmol) in EtOH (20 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). Purification by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9) afforded N-{2-[(4-bromobenzyloxyimino)phenylmethyl]-4-chlorophenyl}trifluoromethanesulfonamide 64 (210 mg, 38%), as a yellow solid. M.p. 55-56° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.32, br s, 1H, 7.66, d, J=9.0 Hz, 1H, 7.55-7.48, m, 5H, 7.33-7.20, m, 5H, 6.88, d, J=2.4 Hz, 1H, 5.11, s, 2H. The reaction mixture was concentrated under vacuum 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)