Potassium Carbonate → HCID 178441578, compound

HRID 2389279Notes

Reaction equation

HRID 2389279 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4](=O)[CH2:5]Br.[CH3:12][C:13]([C:16]([NH2:18])=[NH:17])([CH3:15])[CH3:14].Cl.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>C(#N)C>[C:13]([C:16]1[NH:17][CH:5]=[C:4]([C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=2[Cl:1])[N:18]=1)([CH3:15])([CH3:14])[CH3:12]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 27357852-Bromo-2'-chloroacetophenoneHCID 2781880Propanimidamide, 2,2-dimethyl-, hydrochloride (1:1)

Product 1

HCID 178441578HCID 178441578, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-chlorophenacyl bromide (310 mg, 1.33 mmol), tert-butylcarbamidine hydrochloride (210 mg, 1.53 mmol), potassium carbonate (0.420 mg, 3.04 mmol), and acetonitrile (6 mL) was refluxed at 90° C. for 3 hours. After the mixture was left to cool to room temperature, an aqueous sodium hydrogen carbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under reduced pressure to give 2-tert-butyl-4-(2-chlorophenyl)-1H-imidazole (132 mg, 0.56 mmol, yield: 42%).

Workup

  1. waitAfter the mixture was left
  2. temperatureto cool to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThen, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-338712e03a7e460a9e8381d60b96ddd3
Source dataset
uspto-grants-2012_09
Patent number
US08273738B2

Reaction notes

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