Imidazole → 4-[(4-Chlorophenyl)sulfanyl]-1-(1H-imidazol-1-yl)-3,3-dimethylbutan-2-one

HRID 544522Notes

Reaction equation

HRID 544522 reaction equation
Br[CH2:2][C:3](=[O:16])[C:4]([CH3:15])([CH3:14])[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([S:6][CH2:5][C:4]([CH3:15])([CH3:14])[C:3](=[O:16])[CH2:2][N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 127659741-Bromo-4-[(4-chlorophenyl)sulfanyl]-3,3-dimethylbutan-2-one

Product 1

HCID 130649584-[(4-Chlorophenyl)sulfanyl]-1-(1H-imidazol-1-yl)-3,3-dimethylbutan-2-oneYield 82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

199 g (0.618 mol) of 1-bromo-4-(4-chlorophenylsulphenyl)-3,3-dimethylbutan-2-one, 120 g (1.76 mols) of imidazole and 243.5 g (1.76 mols) of potassium carbonate in 3 liters of acetone are stirred under reflux for 5 hours. The mixture is then allowed to cool, the inorganic salts are filtered off with suction, and the filtrate is concentrated. The residue is taken up in methylene chloride, washed three times with water, dried over sodium sulphate, and concentrated. Recrystallizing from diisopropyl ether produces 156 g (82% of theory) of 4-(4-chlorophenylsulphenyl)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-one having a melting point of 50° C. ##STR118##

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureto cool
  3. filtrationthe inorganic salts are filtered off with suction
  4. concentrationthe filtrate is concentrated
  5. washwashed three times with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. customRecrystallizing from diisopropyl ether

Sources & evidence

ORD record
ord-a3748a068bcf4cabb6a461d1476c8fb3
Source dataset
uspto-grants-1984_05
Patent number
US04451281

Reaction notes

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