Ethanol → 3-(1-(1H)-Imidazolyl)-1-(3-trifluoromethylphenyl)-1-propanone O-(2-aminoethyl)oxime dihydrochloride

HRID 2293084노트

반응식

HRID 2293084 반응식
[N:1]1([CH2:6][CH2:7][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=O)[CH:5]=[CH:4][N:3]=[CH:2]1.[ClH:20].Cl.[NH2:22][CH2:23][CH2:24][O:25][NH2:26].N1C=CC=CC=1.C(O)C>[OH-].[Na+].C(OCC)(=O)C>[ClH:20].[ClH:20].[NH2:22][CH2:23][CH2:24][O:25][N:26]=[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1)[CH2:7][CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

참가 물질

7

반응물 4

HCID 702EthanolHCID 1049PyridineHCID 143623262-(O-aminooxy)ethylamine dihydrochlorideHCID 190783313-(1-(1H)-imidazolyl)-1-(3-trifluoromethylphenyl)-1-propanone

생성물 1

HCID 867510593-(1-(1H)-Imidazolyl)-1-(3-trifluoromethylphenyl)-1-propanone O-(2-aminoethyl)oxime dihydrochloride수율 53.5%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매

실험 절차

A mixture of 3-(1-(1H)-imidazolyl)-1-(3-trifluoromethylphenyl)-1-propanone (4.60 g), O-(2-aminoethyl)hydroxylamine dihydrochloride (3.07 g), 3 equivalents of pyridine, and absolute ethanol (75 ml) was stirred under reflux, under nitrogen, for three hrs. The reaction mixture was diluted with 10% sodium hydroxide solution and ethyl acetate. The layers were separated. The aqueous phase was extracted with ethyl acetate, the organic layers were dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated. The residue was taken up in toluene and evaporated. The residue was flash chromatographed (180:19:1 dichloromethane/methanol/ammonium hydroxide). The appropriate fractions were collected and concentrated. The residue was dissolved in absolute ethanol and treated with ethereal hydrogen chloride. Diethyl ether was added to the solution. The solid was collected and recrystallized twice from absolute ethanol/ether to give 2.2 g (32%) of product, mp 223°-225° C. (dec.)

후처리

  1. temperatureunder reflux, under nitrogen, for three hrs
  2. customThe layers were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialthe organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated
  7. customevaporated
  8. customchromatographed (180:19:1 dichloromethane/methanol/ammonium hydroxide)
  9. customThe appropriate fractions were collected
  10. concentrationconcentrated
  11. dissolutionThe residue was dissolved in absolute ethanol
  12. additiontreated with ethereal hydrogen chloride
  13. additionDiethyl ether was added to the solution
  14. customThe solid was collected
  15. customrecrystallized twice from absolute ethanol/ether

출처 및 근거

ORD 기록
ord-21a4970b1005491b81c0026125f027c9
출처 데이터셋
uspto-grants-1997_11
특허 번호
US05686447

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