Sodium Acetate → N-{2-[(2,4-bistrifluoromethylbenzyloxyimino)methyl]-4-chlorophenyl}-trifluoromethanesulfonamide

HRID 602611ノート

反応式

HRID 602611 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.[F:19][C:20]([F:35])([F:34])[C:21]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:22]=1[CH2:23][O:24][NH2:25].CC([O-])=O.[Na+]>CCO>[F:19][C:20]([F:34])([F:35])[C:21]1[CH:29]=[C:28]([C:30]([F:33])([F:31])[F:32])[CH:27]=[CH:26][C:22]=1[CH2:23][O:24][N:25]=[CH:16][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[NH:8][S:9]([C:12]([F:13])([F:14])[F:15])(=[O:10])=[O:11]

参加物

5

反応物 3

HCID 517045Sodium AcetateHCID 86230463O-(2,4-bistrifluoromethylbenzyl)hydroxylamine hydrochlorideHCID 86230476N-(4-chloro-2-formylphenyl)trifluoromethanesulfonamide

生成物 1

HCID 86604006N-{2-[(2,4-bistrifluoromethylbenzyloxyimino)methyl]-4-chlorophenyl}-trifluoromethanesulfonamide収率 58%

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 (180 mg, 0.63 mmol), O-(2,4-bistrifluoromethylbenzyl)hydroxylamine hydrochloride (342 mg, 1.16 mmol) and anhydrous NaOAc (141 mg, 1.72 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 to 3:7) afforded N-{2-[(2,4-bistrifluoromethylbenzyloxyimino)methyl]-4-chlorophenyl}-trifluoromethanesulfonamide 65 (192 mg, 58%), as a yellow solid. M.p. 65-67° C. 1H n.m.r. (200 MHz, CDCl3) δ 10.38, br s, 1H, 8.20, s, 1H, 7.97, s, 1H, 7.86, d, J=8.0 Hz, 1H, 7.75, d, J=8.0 Hz, 1H; 7.65, d, J=8.8 Hz, 1H, 7.35, dd, J=2.4 and 8.8 Hz, 1H, 7.28, d, J=2.4 Hz, 1H, 5.44, s, 2H.

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 to 3:7)

出典と根拠

ORDレコード
ord-5ab1cdd27a154dd8a2578928cea44582
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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