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

HRID 856804
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인쇄 미리보기

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HRID 856804 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 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

시약·촉매·용매 1

HCID 702
Ethanol
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c1921629dd274c1c82099d045871b295
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07262185B2

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