Hydrogen Peroxide → HCID 66667011, compound

HRID 1620327Notes

Reaction equation

HRID 1620327 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:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:10][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:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 66666788HCID 66666788, compound

Product 1

HCID 66667011HCID 66667011, compoundYield 145.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium carbonate (0.143 g, 1.0 mmol) was added to a solution of 4-(4-chlorophenoxy)-3-(3-methoxypyridin-2-yl)benzonitrile (Preparation 12, 0.175 g, 0.52 mmol) in DMSO, followed by dropwise addition of 30% hydrogen peroxide aqueous solution (3.1 mL, 3.1 mmol). The mixture was stirred at room temperature for 1.5 hours. The reaction was quenched with aqueous potassium hydrogen sulfate (30 mL) and extracted with DCM (3×30 mL). The organic layer was washed with water (2×30 mL), dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a white solid (0.269 g). This was taken to the next step without further purification.

Workup

  1. customThe reaction was quenched with aqueous potassium hydrogen sulfate (30 mL)
  2. extractionextracted with DCM (3×30 mL)
  3. washThe organic layer was washed with water (2×30 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-33b36818a59c4ef682fa6128be7065bf
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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