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

HRID 1377734
Notes
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Reaction equation

HRID 1377734 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents

2
HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

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.)

Workup

  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

Sources & evidence

ORD record
ord-79fda123e64f49b58293db9d567e170d
Source dataset
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05665756

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes