Imidazole → HCID 53895873, compound

HRID 1153949Notes

Reaction equation

HRID 1153949 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-pentan-2-one in 200 ml of toluene are added to this mixture at 80° C. The reaction mixture is stirred for a further 10 hours at 90° C., cooled and filtered off under suction from the inorganic residue. The filtrate is washed with water, dried over sodium sulphate and evaporated down. 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. temperaturecooled
  2. filtrationfiltered off under suction from the inorganic residue
  3. washThe filtrate is washed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated down
  6. customThe residue is purified by column chromatography (silica gel: ethyl acetate/cyclohexane=3/1)

Sources & evidence

ORD record
ord-39b79da91bd0499a88acb27159ff466c
Source dataset
uspto-grants-1984_12
Patent number
US04487776

Reaction notes

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