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

HRID 970872노트

반응식

HRID 970872 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-7ba924807db6498998aaa93886b3c309
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312248B2

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