Imidazole → HCID 54480835, compound

HRID 638600Notes

Reaction equation

HRID 638600 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:13]([S: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]([S: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 13556593HCID 13556593, compound

Product 1

HCID 54480835HCID 54480835, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

64.9 g (0.94 mole) of imidazole and 129.7 g (0.94 mole) of potassium carbonate are dissolved in 1,300 ml of toluene. 173.9 g (0.47 mole) of 1-bromo-1-(4-chlorophenylthio)-5-chloro-3,3-dimethyl-2-pentanone in 360 ml of toluene are added dropwise to this mixture at 80° C. The reaction mixture is subsequently stirred at 90° C. for 15 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 recrystallized from diethyl ether. 61.4 g (40.8% of theory) of 4-chlorophenylthio-(imidazol-1-yl)-(3,3-dimethyl-tetrahydrofuran-2-ylidene)-methane of melting point 134° 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 recrystallized from diethyl ether

Sources & evidence

ORD record
ord-f867e8f36f664911822c7e18f505d242
Source dataset
uspto-grants-1985_12
Patent number
US04562198

Reaction notes

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