Imidazole → HCID 14798983, compound

HRID 345863Notes

Reaction equation

HRID 345863 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[C:6]([C:8]1([C:11]2([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH2:13][O:12]2)[CH2:10][CH2:9]1)#[N:7]>C(#N)C>[C:6]([C:8]1([C:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)([OH:12])[CH2:13][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH2:9][CH2:10]1)#[N:7]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 14798965HCID 14798965, compound

Product 1

HCID 14798983HCID 14798983, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4 g (59 mmol) of imidazole and 2.1 g (10 mmol) of 2-(1-cyanocyclopropyl)-2-(4-fluorophenyl)oxirane (IV-2, Example 33) in 20 ml of abs. acetonitrile are heated under reflux for 8 h under a nitrogen atmosphere. After evaporation of the solvent in vacuo, the residue is taken up in ethyl acetate. The mixture is washed with water and dried over Na2SO4, and the solvent is evaporated in vacuo. Chromatographic purification on silica gel (eluent: dichloromethane containing 2% ethanol) gives 1.1 g (39% of theory) of 1-(1-cyanocyclopropyl)-1-(4-fluorophenyl)-2 -(imidazol-1-yl)ethanol having a melting point of 173° C. (dec.), 1H--NMR (CDCl3):

Workup

  1. temperatureunder reflux for 8 h under a nitrogen atmosphere
  2. customAfter evaporation of the solvent in vacuo
  3. washThe mixture is washed with water
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated in vacuo
  6. customChromatographic purification on silica gel (eluent: dichloromethane containing 2% ethanol)

Sources & evidence

ORD record
ord-65865e6259bf41c6a5babed2c40f4843
Source dataset
uspto-grants-1991_10
Patent number
US05059615

Reaction notes

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