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Ethanol → 4-(2-Methyl-1-(1H)-imidazolyl)-1-(4-trifluoromethylphenyl)-1-butanone O-(2-aminoethyl)oxime dihydrochloride

HRID 964750
Notes
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Reaction equation

HRID 964750 reaction equation
[CH3:1][C:2]1[N:3]([CH2:7][CH2:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=O)[CH:4]=[CH:5][N:6]=1.[ClH:22].Cl.[NH2:24][CH2:25][CH2:26][O:27][NH2:28].N1C=CC=CC=1.C(O)C>[OH-].[Na+].C(OCC)(=O)C>[ClH:22].[ClH:22].[NH2:24][CH2:25][CH2:26][O:27][N:28]=[C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)[CH2:9][CH2:8][CH2:7][N:3]1[CH:4]=[CH:5][N:6]=[C:2]1[CH3:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 143623262-(O-aminooxy)ethylamine dihydrochlorideHCID 190783264-(2-methyl-1-(1H)-imidazolyl)-1-(4-trifluoromethylphenyl)-1-butanone

Product 1

HCID 867510624-(2-Methyl-1-(1H)-imidazolyl)-1-(4-trifluoromethylphenyl)-1-butanone O-(2-aminoethyl)oxime dihydrochlorideYield 61%

Reagents, catalysts & solvents

2
HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 4-(2-methyl-1-(1H)-imidazolyl)-1-(4-trifluoromethylphenyl)-1-butanone (2.65 g), O-(2-aminoethyl)hydroxylamine dihydrochloride (1.60 g), 3 equivalents of pyridine, and absolute ethanol (75 nil) was heated under reflux, under nitrogen, with stirring, 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 purified by flash chromatography (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. The precipitate was collected and recrystallized from absolute ethanol/ether to give 1.4 g (37%) of product, mp 181°-184° 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. customThe residue was purified by flash chromatography (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
  15. customThe precipitate was collected
  16. customrecrystallized from absolute ethanol/ether

Sources & evidence

ORD record
ord-efcbe1c20f3845419ef40503d9c0b0ec
Source dataset
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05770740

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes