Imidazole → HCID 54031528, compound

HRID 638610Notes

Reaction equation

HRID 638610 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[Cl:12][C:13]1[CH:30]=[CH:29][C:16]([O:17][CH:18](Br)[C:19](=[O:27])[C:20]([CH3:26])([CH3:25])[CH:21]([Br:24])[CH2:22]Br)=[CH:15][CH:14]=1.O>C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:30]=[CH:29][C:16]([O:17][C:18]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[C:19]2[C:20]([CH3:26])([CH3:25])[CH:21]([Br:24])[CH2:22][O:27]2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 11430Potassium CarbonateHCID 13556595HCID 13556595, compound

Product 1

HCID 54031528HCID 54031528, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

35 g (0.5 mole) of imidazole and 103.5 g (0.75 mole) of potassium carbonate are dissolved in 700 ml of toluene at 60° C. 132 g (0.269 mole) of 1-(4-chlorophenoxy)-3,3-dimethyl-1,4,5-tribromo-2-pentanone in 100 ml of toluene are added dropwise to this solution in the course of 20 minutes. The reaction mixture is subsequently stirred at 90° C. for 10 hours and cooled and water is added. The organic phase is separated off, washed with water dried over sodium sulphate and concentrated. The residue is purified by column chromatography (silica gel; ethyl acetate/cyclohexane=3:1). 10.6 g (10% of theory) of (4-chlorophenoxy)-(imidazol-1-yl)-(4-bromo-3,3-dimethyltetrahydrofuran-2-ylidene)-methane of refractive index nD20 1.5837 are obtained.

Workup

  1. temperaturecooled
  2. customThe organic phase is separated off
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography (silica gel; ethyl acetate/cyclohexane=3:1)

Sources & evidence

ORD record
ord-e40f6f0804c6467681bfec2f9fd163bc
Source dataset
uspto-grants-1985_12
Patent number
US04562198

Reaction notes

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