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Hydroxyamine hydrochloride → (1Z)-2-(4-aminophenyl)-1-(1-propylimidazol-2-yl)ethanone oxime

HRID 856804
ノート
印刷プレビュー

反応式

HRID 856804 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[N:12]([CH2:16][CH2:17][CH3:18])[CH:13]=[CH:14][N:15]=2)=O)=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21].C(=O)(O)[O-].[Na+]>C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]/[C:9](/[C:11]2[N:12]([CH2:16][CH2:17][CH3:18])[CH:13]=[CH:14][N:15]=2)=[N:20]\[OH:21])=[CH:4][CH:3]=1.[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]/[C:9](/[C:11]2[N:12]([CH2:16][CH2:17][CH3:18])[CH:13]=[CH:14][N:15]=2)=[N:20]/[OH:21])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 229387292-(4-Aminophenyl)-1-(1-propylimidazol-2-yl)ethanone

生成物 2

HCID 135829454(1Z)-2-(4-aminophenyl)-1-(1-propylimidazol-2-yl)ethanone oximeHCID 136334097(1E)-2-(4-aminophenyl)-1-(1-propylimidazol-2-yl)ethanone oxime

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

実験手順

A solution of 2-(4-aminophenyl)-1-(1-propylimidazol-2-yl)ethanone (400 mg) and hydroxylamine hydrochloride (149 mg) in ethanol (15 ml) was refluxed for 1 day. The mixture was allowed to be at room temperature, saturated sodium bicarbonate solution was added to the mixture, extracted with ethyl acetate, and washed with saturated brine. The mixture was dried over magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=1:1→ethyl acetate) and recrystallized from hexane-ethyl acetate, to give (1E)-2-(4-aminophenyl)-1-(1-propylimidazol-2-yl)ethanone oxime (220 mg) and (1Z)-2-(4-aminophenyl)-1-(1-propylimidazol-2-yl)ethanone oxime (58 mg) as pale red crystals.

後処理

  1. customto be at room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialThe mixture was dried over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=1:1→ethyl acetate)
  7. customrecrystallized from hexane-ethyl acetate

出典と根拠

ORDレコード
ord-c1921629dd274c1c82099d045871b295
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07262185B2

反応ノート

読み込み中…

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