Imidazole → HCID 131712418, compound

HRID 1578104Notes

Reaction equation

HRID 1578104 reaction equation
Cl[CH:2]=[C:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6].N1C=CN=C1.[Na].C[O-].[Na+].N1C=CN=C1>C(#N)C.CO>[F:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][C:3]([C:4](=[O:9])[C:5]([CH3:6])([CH3:7])[CH3:8])=[CH2:2])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 10942334Sodium MethoxideHCID 54381910HCID 54381910, compoundHCID 57373095Imidazole sodium

Product 1

HCID 131712418HCID 131712418, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent2×

Procedure

256.7 g (1 mol) of 1-chloro-2-(4-fluorophenoxy)-4,4-dimethyl-penten-3-one in 150 ml of acetonitrile were added dropwise to a suspension of 90 g (1 mol) of sodium imidazole, prepared from sodium methylate and imidazole in methanol, in 2,5000 ml of acetonitrile, while stirring. Thereafter, the reaction mixture was heated to the boil for 6 hours. It was allowed to cool to room temperature and was concentrated by distilling off the solvent in vacuo. The residue was taken up in 1,000 ml of ethyl acetate, the ethyl acetate mixture was washed three times with 200 ml of water each time and the organic phase was dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. 272.4 g (94.5% of theory) of crude 1-imidazol-1-yl)-2-(4-fluorophenoxy)-4,4-dimethyl-penten-3-one were obtained as a brown oil.

Workup

  1. temperatureThereafter, the reaction mixture was heated to the boil for 6 hours
  2. concentrationwas concentrated
  3. distillationby distilling off the solvent in vacuo
  4. washthe ethyl acetate mixture was washed three times with 200 ml of water each time
  5. dry with materialthe organic phase was dried over sodium sulphate
  6. concentrationconcentrated
  7. distillationby distilling off the solvent in vacuo

Sources & evidence

ORD record
ord-0d452e1f49e14f258939b8fe133ca423
Source dataset
uspto-grants-1981_09
Patent number
US04291044

Reaction notes

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