Hydrogen Peroxide → HCID 66666715, compound

HRID 1620318Notes

Reaction equation

HRID 1620318 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].[Cl:7][C:8]1[CH:30]=[CH:29][C:11]([O:12][C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=2[C:21]2[C:22]([O:27][CH3:28])=[N:23][CH:24]=[CH:25][CH:26]=2)=[C:10]([O:31][CH3:32])[CH:9]=1.OO>CS(C)=O>[Cl:7][C:8]1[CH:30]=[CH:29][C:11]([O:12][C:13]2[CH:20]=[CH:19][C:16]([C:17]([NH2:18])=[O:2])=[CH:15][C:14]=2[C:21]2[C:22]([O:27][CH3:28])=[N:23][CH:24]=[CH:25][CH:26]=2)=[C:10]([O:31][CH3:32])[CH:9]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 66666696HCID 66666696, compound

Product 1

HCID 66666715HCID 66666715, compoundYield 113.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium carbonate (0.194 g, 1.40 mmol) was added to a solution of 4-(4-chloro-2-methoxyphenoxy)-3-(2-methoxypyridin-3-yl)benzonitrile (Preparation 2, 0.257 g, 0.701 mmol) in dimethylsulfoxide (6 mL), followed by dropwise addition of 30% hydrogen peroxide aqueous solution (0.422 mL, 14.00 mmol). The mixture was stirred at room temperature for 1 hour, then quenched by addition of saturated aqueous solution of ammonium chloride (20.0 mL) and water (20.0 mL). The pH of the aqueous was adjusted to pH=7 by dropwise addition of saturated aqueous solution of potassium hydrogen sulfate and then extracted with DCM (3×20 mL). The combined organics were washed with brine (50 mL) and filtered to give the title compound as a solid (0.307 g).

Workup

  1. customquenched by addition of saturated aqueous solution of ammonium chloride (20.0 mL) and water (20.0 mL)
  2. additionThe pH of the aqueous was adjusted to pH=7 by dropwise addition of saturated aqueous solution of potassium hydrogen sulfate
  3. extractionextracted with DCM (3×20 mL)
  4. washThe combined organics were washed with brine (50 mL)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-1a715c96005249b4907951363dd45b6e
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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