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

HRID 602617ノート

反応式

HRID 602617 の反応式
[C:1]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[NH:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])(=O)[CH2:2][CH2:3][CH3:4].Cl.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][NH2:30])=[CH:25][CH:24]=1.CC([O-])=O.[Na+]>CCO>[Cl:12][C:10]1[CH:9]=[CH:8][C:7]([NH:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])=[C:6]([C:1](=[N:30][O:29][C:26]2[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=2)[CH2:2][CH2:3][CH3:4])[CH:11]=1

参加物

5

反応物 3

HCID 517045Sodium AcetateHCID 20445467O-(4-chlorophenyl)hydroxylamine hydrochlorideHCID 67270216N-(2-butyryl-4-chlorophenyl)trifluoromethanesulfonamide

生成物 1

HCID 73021830N-{4-chloro-2-[1-(4-chlorophenoxyimino)butyl]phenyl}trifluoromethanesulfonamide収率 62.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of N-(2-butyryl-4-chlorophenyl)trifluoromethanesulfonamide 29A (333 mg, 1.0 mmol), O-(4-chlorophenyl)hydroxylamine hydrochloride (200 mg, 1.10 mmol) and anhydrous NaOAc (91 mg, 1.10 mmol) in EtOH (30 mL) was stirred for 15 hours at RT. The reaction mixture was concentrated under vacuum, the residue filtered through a pad of silica (eluting with CH2Cl2/PE, 1:4) and the solvent removed under reduced pressure. The residue was purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:19 to 3:7) to afford N-{4-chloro-2-[1-(4-chlorophenoxyimino)butyl]phenyl}trifluoromethanesulfonamide 166 (283 mg, 62%), as a yellow solid. M.p. 62.5-64.5° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.27, br s, 1H, 7.72, d, J=8.8 Hz, 1H; 7.57d, J=2.4 Hz, 1H, 7.41, dd, J=2.4 and 8.8 Hz, 1H; 7.35, d, J=8.8 Hz, 2H, 7.11, d, J=8.8 Hz, 2H; 2.98, m, 2H, 1.71, sextet, 2H, 1.09, t, J=7.4 Hz,

後処理

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. filtrationthe residue filtered through a pad of silica (eluting with CH2Cl2/PE, 1:4)
  3. customthe solvent removed under reduced pressure
  4. customThe residue was purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:19 to 3:7)

出典と根拠

ORDレコード
ord-875e67a5a25e445bb434e55ee4bfdb03
出典データセット
uspto-grants-2011_03
特許番号
US07906538B2

反応ノート

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