Ethanol → 3-(1-(1H)-Imidazolyl)-1-(4-trifluoromethylphenyl)-1-propanone O-(2-aminoethyl)oxime dihydrochloride

HRID 265269Notes

Reaction equation

HRID 265269 reaction equation
[N:1]1([CH2:6][CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][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][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)[CH2:7][CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 143623262-(O-aminooxy)ethylamine dihydrochlorideHCID 190783383-(1-(1H)-imidazolyl)-1-(4-trifluoromethylphenyl)1-propanone

Product 1

HCID 737929053-(1-(1H)-Imidazolyl)-1-(4-trifluoromethylphenyl)-1-propanone O-(2-aminoethyl)oxime dihydrochlorideYield 67.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 3-(1-(1H)-imidazolyl)-1-(4-trifluoromethylphenyl)1-propanone (4.65 g), O-(2-aminoethyl)hydroxylamine dihydrochloride (3.10 g), 3 equivalents of pyridine, and absolute ethanol (75 ml) was heated under reflux, under nitrogen, with stirring, for two 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 2.8 g (40%) of product, mp 213°-214° C. (dec).

Workup

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

Sources & evidence

ORD record
ord-9bd13fa869a94d398735b8e4196b8804
Source dataset
uspto-grants-1997_07
Patent number
US05648367

Reaction notes

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