Imidazole → HCID 118555039, compound

HRID 1051289Notes

Reaction equation

HRID 1051289 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].[C:11]1([OH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[H-].[Na+].[NH:26]1[CH:30]=[CH:29][N:28]=[CH:27]1>CS(C)=O.O>[N:26]1([C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[O:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]#[N:6])[CH:30]=[CH:29][N:28]=[CH:27]1

Participants

8

Reactant 5

HCID 795ImidazoleHCID 996PhenolHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 1455253-Chloro-4-fluorobenzonitrile

Product 1

HCID 118555039HCID 118555039, compoundYield 49.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A reaction mixture solution prepared by suspending 77.8 mg of 3-chloro-4-fluorobenzonitrile, 51.8 mg of phenol and 82.9 mg of potassium carbonate in 2 mL of dimethylsulfoxide was heated at 100° C. for 14 hours under a nitrogen atmosphere. Subsequently, 24.0 mg of sodium hydride and 40.8 mg of imidazole were added to the reaction mixture solution, and the mixture was heated at 140° C. for 5 hours under a nitrogen atmosphere. After the addition of water to the reaction mixture solution, extraction was performed using ethyl acetate. The organic phase is washed with saline, followed by drying and concentrating under reduced pressure. The resulting crude product was separated and purified by silica gel column chromatography to obtain 65.2 mg of 3-(1H-imidazol-1-yl)-4-phenoxybenzonitrile.

Workup

  1. customA reaction mixture solution prepared
  2. temperaturethe mixture was heated at 140° C. for 5 hours under a nitrogen atmosphere
  3. extractionto the reaction mixture solution, extraction
  4. washThe organic phase is washed with saline
  5. customby drying
  6. concentrationconcentrating under reduced pressure
  7. customThe resulting crude product was separated
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-119e683b191e497c998b518a5241e1fd
Source dataset
uspto-grants-2016_07
Patent number
US09388174B2

Reaction notes

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