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

HRID 602612ノート

反応式

HRID 602612 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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) δ10.65, 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.

後処理

  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)

出典と根拠

ORDレコード
ord-ea1e3b94c8394ae6b685956ede466a1c
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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