Sodium Acetate → 4-Chloro-2-[(3,4-dichlorobenzyloxyimino)phenylmethyl]phenyltrifluoromethanesulfonamide

HRID 970872ノート

反応式

HRID 970872 の反応式
[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[Cl:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:29][O:30][NH2:31].CC([O-])=O.[Na+]>CCO>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]([NH:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])=[C:9]([C:1](=[N:31][O:30][CH2:29][C:28]2[CH:32]=[CH:33][C:34]([Cl:35])=[C:26]([Cl:25])[CH:27]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=1

参加物

5

反応物 3

HCID 517045Sodium AcetateHCID 21683122O-(3,4-Dichlorobenzyl)hydroxylamine hydrochlorideHCID 67271057N-(2-benzoyl-4-chlorophenyl)trifluoromethanesulfonamide

生成物 1

HCID 866040084-Chloro-2-[(3,4-dichlorobenzyloxyimino)phenylmethyl]phenyltrifluoromethanesulfonamide収率 51%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of N-(2-benzoyl-4-chlorophenyl)trifluoromethanesulfonamide 25 (710 mg, 1.95 mmol), O-(3,4-dichlorobenzyl)hydroxylamine hydrochloride (468 .mg, 2.05 mmol) and anhydrous NaOAc (168 mg, 2.05 mmol) in EtOH (50 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, 3:2) and the solvent removed under reduced pressure. An isomeric mixture of E- and Z-oxime ether derivatives was obtained, which were separated by radial thin layer chromatography (eluting with CH2Cl2/PE, 7.5:92.5 to 1:5). The major isomer was obtained as a pale yellow solid which was recrystallized from CH2Cl2/PE to give N-{4-chloro-2-[(3,4-dichlorobenzyloxyimino)phenylmethyl]phenyl}trifluoromethanesulfonamide 87 (535 mg, 51%), as pale yellow crystals. M.p. 87-88° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.18, br s, 1H; 7.65, d, J=8.8 Hz, 1H; 7.55-7.40, m, 5H; 7.34-7.14, m, 4H; 6.88, d, J=2.2 Hz, 1H; 5.09, s, 2H. The minor isomer was obtained as a pale yellow solid (315 mg, 30%).

後処理

  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 solvent removed under reduced pressure
  4. additionAn isomeric mixture of E- and Z-oxime ether derivatives
  5. customwas obtained
  6. customwhich were separated by radial thin layer chromatography (eluting with CH2Cl2/PE, 7.5:92.5 to 1:5)
  7. customThe major isomer was obtained as a pale yellow solid which
  8. customwas recrystallized from CH2Cl2/PE

出典と根拠

ORDレコード
ord-7ba924807db6498998aaa93886b3c309
出典データセット
uspto-grants-2007_12
特許番号
US07312248B2

反応ノート

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