Potassium Carbonate → HCID 18920171, compound

HRID 1291048Notes

Reaction equation

HRID 1291048 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[C:10]1([C:16]2[NH:17][CH:18]=[CH:19][N:20]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[C:10]1([C:16]2[N:20]([C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=3)[CH:19]=[CH:18][N:17]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 695912-Phenylimidazole

Product 1

HCID 18920171HCID 18920171, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluorobenzonitrile (3.63 g, 30 mmol), 2-phenylimidazole (3.72 g, 30 mmol) and anhydrous K2CO3 (4.15 g, 30 mmol) in dry DMSO (30 ml) was heated at 100° C. for 20 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was poured into an ice-cold saturated aqueous NH4Cl (100 ml) solution and the whole extracted with Et2O (150 ml×2). The combined extracts was washed with water (100 ml), brine (80 ml), dried over MgSO4 and solvent removed under reduced pressure. The resultant residue was purified by column chromatography (SiO2 ; dichloromethane:ethyl acetate:ethanol=20:1:1) to afford title compound (3.61 g, 49%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe whole extracted with Et2O (150 ml×2)
  3. washThe combined extracts was washed with water (100 ml), brine (80 ml)
  4. dry with materialdried over MgSO4 and solvent
  5. customremoved under reduced pressure
  6. customThe resultant residue was purified by column chromatography (SiO2 ; dichloromethane:ethyl acetate:ethanol=20:1:1)

Sources & evidence

ORD record
ord-a3dfe9f6ae8e4d41ac61efc10aa2a68d
Source dataset
uspto-grants-1998_05
Patent number
US05753682

Reaction notes

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