Sodium Acetate → N-{4-chloro-2-[(3,4-dichlorobenzyloxyimino)methyl]phenyl}trifluoromethanesulfonamide

HRID 970870노트

반응식

HRID 970870 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[C:4]([CH:16]=O)[CH:3]=1.Cl.[Cl:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:23][O:24][NH2:25].CC([O-])=O.[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]([F:13])([F:14])[F:15])(=[O:10])=[O:11])=[C:4]([CH:16]=[N:25][O:24][CH2:23][C:22]2[CH:26]=[CH:27][C:28]([Cl:29])=[C:20]([Cl:19])[CH:21]=2)[CH:3]=1

참가 물질

5

반응물 3

HCID 517045Sodium AcetateHCID 21683122O-(3,4-Dichlorobenzyl)hydroxylamine hydrochlorideHCID 86230476N-(4-chloro-2-formylphenyl)trifluoromethanesulfonamide

생성물 1

HCID 86604007N-{4-chloro-2-[(3,4-dichlorobenzyloxyimino)methyl]phenyl}trifluoromethanesulfonamide수율 66%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of N-(4-chloro-2-formylphenyl)trifluoromethanesulfonamide 24 (163 mg, 0.57 mmol), O-(3,4-dichlorobenzyl)hydroxylamine hydrochloride (130 mg, 0.57 mmol) and anhydrous NaOAc (77 mg, 0.94 mmol) in EtOH (10 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 CHCl3). Purification by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9) afforded N-{4-chloro-2-[(3,4-dichlorobenzyloxyimino)methyl]phenyl}trifluoromethanesulfonamide 97 (172 mg, 66%), as a colorless oil. 1H n.m.r. (200 MHz, CDCl3) δ 10.65, br s, 1H; 8.14, s, 1H; 7.66, d, J=8.8 Hz, 1H; 7.51-7.45, m, 2H; 7.35, dd, J=2.4 and 8.8 Hz, 1H; 7.27-7.22, m, 2H; 5.12, s, 2H. HRMS (M+) 459.9422.

후처리

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. filtrationthe residue filtered through a pad of silica (eluting with CHCl3)
  3. customPurification
  4. washby radial thin layer chromatography (eluting with CH2Cl2/PE, 1:9)

출처 및 근거

ORD 기록
ord-f757246c592c46d29e7b35bb487803e4
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312248B2

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