Chloroform → HCID 178489321, compound

HRID 2356699Notes

Reaction equation

HRID 2356699 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])=O.Cl.[F:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=[NH:20])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)Cl>C(#N)C.O>[F:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]2[NH:20][CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[O:11][CH3:12])[N:21]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 123440Bromomethyl 2-methoxyphenyl ketoneHCID 124561604-Fluorobenzamidine Hydrochloride

Product 1

HCID 178489321HCID 178489321, compoundYield 255.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromo-2′-methoxy-acetophenone (514 mg), 4-fluorobenzamidine hydrochloride (392 mg) and potassium carbonate (930 mg) in acetonitrile (5 ml) was refluxed for 2 hours. After cooling, to the reaction mixture were added chloroform and water, the organic layer was collected and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was recrystallized from methanol to obtain 2-(4-fluorophenyl)-4-(2-methoxyphenyl)imidazole (1.54 g) as pale yellowish crystal. This compound was treated with hydrogen chloride-ethanol solution to be converted into a hydrochloride salt form.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter cooling, to the reaction mixture
  3. customthe organic layer was collected
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe resulting residue was recrystallized from methanol

Sources & evidence

ORD record
ord-a5bc164c565c4dc89bab97ef61670652
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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