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3-Bromo-1,1,1-trifluoro-2-propanone → 5-Methyl-2-[4-hydroxy-1-[4-(methylthio)phenyl]-4-(trifluoromethyl)-4.5-dihydro-1h-imidazol-2-yl]pyridine

HRID 1352980
Notes
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Reaction equation

HRID 1352980 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[NH:18])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.C(=O)(O)[O-].[Na+].Br[CH2:25][C:26](=[O:31])[C:27]([F:30])([F:29])[F:28].N1C=CNC1>C(O)(C)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:10]3[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=3)[CH2:25][C:26]([OH:31])([C:27]([F:30])([F:29])[F:28])[N:18]=2)=[N:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 516892Sodium BicarbonateHCID 52325931H-Imidazole, 2,3-dihydro-HCID 178503252HCID 178503252, compound

Product 1

HCID 229980615-Methyl-2-[4-hydroxy-1-[4-(methylthio)phenyl]-4-(trifluoromethyl)-4.5-dihydro-1h-imidazol-2-yl]pyridine

Reagents, catalysts & solvents 1

HCID 3776
Isopropanol
Solvent

Procedure

To a mixture of the amidine of step 2 (10 g, 52.41 mmol) and sodium bicarbonate (8.6 g, 103 mmol) in isopropanol (1200 ml), 3-bromo-1,1,1-trifluoroacetone (10 g, 52 mmol) was added. After heating at reflux for 22 hours, the reaction mixture was cooled and filtered. The residue was dissolved in methylene chloride and washed water than brine. The organic extracts were dried (MgSO4), filtered and concentrated. The crude mixture was purified by chromatography (silica gel, 100% ethyl acetate) to give. the desired dihydro-imidazole (5.1 g): Anal Calc'd. for C17H16N3SOF3: C, 55.58; H, 4.39; N, 11.44. Found: C, 55.54; H, 4.35; N, 11.20.

Workup

  1. additionwas added
  2. temperatureAfter heating
  3. temperatureat reflux for 22 hours
  4. temperaturethe reaction mixture was cooled
  5. filtrationfiltered
  6. dissolutionThe residue was dissolved in methylene chloride
  7. washwashed water than brine
  8. dry with materialThe organic extracts were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude mixture was purified by chromatography (silica gel, 100% ethyl acetate)
  12. customto give

Sources & evidence

ORD record
ord-3c91683b5aee45cfb8db77e87ca2b4ac
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07220770B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes