Imidazole → HCID 53779372, compound

HRID 2198898Notes

Reaction equation

HRID 2198898 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].[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.[Na].C[O-].[Na+].N1C=CN=C1>C(#N)C.CO>[N:18]1([CH:2]=[C:3]([O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:4](=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6])[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

7

Reactant 4

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

Product 1

HCID 53779372HCID 53779372, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent2×

Procedure

256.7 g (1 mol) of 1-chloro-2-(4-fluorophenoxy)-4,4-dimethyl-1-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 2,500 ml of acetonitrile, while stirring. Thereafter, the reaction mixture was heated to the boiling point 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 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-1-penten-3-one were obtained as a brown oil, which was purified in the customary manner, via the nitrate, and then had a refractive index of nD20 =1.5590. ##STR52##

Workup

  1. temperatureThereafter, the reaction mixture was heated to the boiling point for 6 hours
  2. concentrationwas concentrated
  3. distillationby distilling off the solvent in vacuo
  4. washthe 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-ba0217cbbd104b4eb1574b492dcc8ca6
Source dataset
uspto-grants-1982_11
Patent number
US04360528

Reaction notes

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