Imidazole → HCID 53895873, compound

HRID 464391Notes

Reaction equation

HRID 464391 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:13]([O:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:14](=[O:21])[C:15]([CH3:20])([CH3:19])[CH2:16][CH2:17]Cl>C1(C)C=CC=CC=1>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][C:13]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[C:14]2[C:15]([CH3:20])([CH3:19])[CH2:16][CH2:17][O:21]2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 132542811-Bromo-5-chloro-1-(4-chlorophenoxy)-3,3-dimethylpentan-2-one

Product 1

HCID 53895873HCID 53895873, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

35 g (0.5 mol) of imidazole and 70 g (0.5 mol) of potassium carbonate are dissolved in 700 ml of toluene. 93 g (0.26 mol) of 1-bromo-1-(4-chlorophenoxy)-5-chloro-3,3-dimethyl-2-pentanone in 200 ml of toluene are added to this mixture at 80° C. The reaction mixture is subsequently stirred at 90° C. for 10 hours and is cooled and the inorganic residue is filtered off with suction. The filtrate is washed with water, dried over sodium sulphate and concentrated. The residue is purified by column chromatography (silica gel: ethyl acetate/cyclohexane=3/1). 12.6 g (14.2% of theory) of (4-chlorophenoxy)-(imidazol-1-yl)-(3,3-dimethyltetrahydrofuran-2-ylidene)-methane of melting point 85°-88° C. are obtained.

Workup

  1. temperatureis cooled
  2. filtrationthe inorganic residue is filtered off with suction
  3. washThe filtrate is washed 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-b7e7e93e754040ed803dee3e9ed206eb
Source dataset
uspto-grants-1985_10
Patent number
US04547515

Reaction notes

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