Imidazole → HCID 54255184, compound

HRID 638605Notes

Reaction equation

HRID 638605 reaction equation
Br[CH:2]([O:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:3](=[O:11])[C:4]([CH2:9][CH3:10])([CH3:8])[CH2:5][CH2:6]Cl.[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1.C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:2]([N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)=[C:3]2[C:4]([CH2:9][CH3:10])([CH3:8])[CH2:5][CH2:6][O:11]2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 11430Potassium CarbonateHCID 13556594HCID 13556594, compound

Product 1

HCID 54255184HCID 54255184, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

69.9 g (0.19 mole) of 1-bromo-1-(4-chlorophenoxy)-5-chloro-3-ethyl-3-methyl-2-pentanone, 26.2 g (0.38 mole) of imidazole and 52.4 g (0.38 mole) of potassium carbonate in 500 ml of toluene are heated at 90° C. for 10 hours. The reaction mixture is then allowed to cool and is poured onto 500 ml of water. The organic phase is separated off, washed with water, dried over sodium sulphate and concentrated. The residue is purified by column chromatography (ethyl acetate/cyclohexane=3:1). 8.5 g (14% of theory) of (4-chlorophenoxy)-(imidazol-1-yl)-(3-ethyl-3-methyltetrahydrofuran-2-ylidene)-methane of refractive index nD20 1.5552 are obtained.

Workup

  1. temperatureto cool
  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 (ethyl acetate/cyclohexane=3:1)

Sources & evidence

ORD record
ord-596c6034912f4625afef33e4c790cc66
Source dataset
uspto-grants-1985_12
Patent number
US04562198

Reaction notes

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