Hydrogen Peroxide → HCID 117841131, compound

HRID 714862Notes

Reaction equation

HRID 714862 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-:17].[K+].[K+].OO.S([O-])([O-])(=O)=S.[Na+].[Na+]>CS(C)=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]([NH2:15])=[O:17])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 68832310HCID 68832310, compound

Product 1

HCID 117841131HCID 117841131, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-(4-aminophenyl)tetrahydro-2H-pyran-4-carbonitrile (500 mg) obtained in Step B of Example 150 and potassium carbonate (1.0 g) in dimethylsulfoxide (10 mL) was added 30% aqueous hydrogen peroxide (0.65 mL), and the mixture was stirred at room temperature for 10 hr. To the reaction mixture was added saturated aqueous sodium thiosulfate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (380 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-9747114c2aa4452b81c74bbea7e7b318
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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