Sodium Acetate → N-{2-[1-(4-fluorophenoxyimino)ethyl]-5-trifluoromethylphenyl}trifluoromethanesulfonamide

HRID 602624ノート

反応式

HRID 602624 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[NH:14][S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])(=O)[CH3:2].Cl.[F:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][NH2:31])=[CH:26][CH:25]=1.CC([O-])=O.[Na+]>CCO>[F:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][N:31]=[C:1]([C:4]2[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:13])[F:12])=[CH:6][C:5]=2[NH:14][S:15]([C:18]([F:21])([F:19])[F:20])(=[O:17])=[O:16])[CH3:2])=[CH:26][CH:25]=1

参加物

5

反応物 3

HCID 517045Sodium AcetateHCID 22120336O-(4-fluorophenyl)hydroxylamine hydrochlorideHCID 86604010N-(2-acetyl-5-trifluoromethylphenyl)trifluoromethanesulfonamide

生成物 1

HCID 72491699N-{2-[1-(4-fluorophenoxyimino)ethyl]-5-trifluoromethylphenyl}trifluoromethanesulfonamide収率 81%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of N-(2-acetyl-5-trifluoromethylphenyl)trifluoromethanesulfonamide 35 (280 mg, 0.84 mmol), O-(4-fluorophenyl)hydroxylamine hydrochloride (150 mg, 0.92 mmol) and anhydrous NaOAc (75 mg, 0.92 mmol) in EtOH (15 mL) was stirred for 24 hours at RT. The reaction mixture was concentrated under vacuum, the residue purified by column chromatography (eluting with CH2Cl2/PE; 1:1 to 4:1) and the solvent removed under reduced pressure. Recrystallization from CH2Cl2/PE afforded N-{2-[1-(4-fluorophenoxyimino)ethyl]-5-trifluoromethylphenyl}trifluoromethanesulfonamide 200 (300 my, 81%), as colorless crystals. M.p. 95-96° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.48, br s, 1H, 8.01, s, 1H, 7.76, d, J=8.4 Hz, 1H, 7.55, m, 1H, 7.19-7.04, m, 4H, 2.60, s, 3H.

後処理

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue purified by column chromatography (eluting with CH2Cl2/PE; 1:1 to 4:1)
  3. customthe solvent removed under reduced pressure
  4. customRecrystallization from CH2Cl2/PE

出典と根拠

ORDレコード
ord-f1e356611dff4e69b6c724dc7794efa9
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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