Hydrogen Peroxide → HCID 67452926, compound

HRID 1474100Notes

Reaction equation

HRID 1474100 reaction equation
[F:1][CH:2]([F:15])[O:3][C:4]1[N:9]=[C:8]([C:10]([CH3:14])([CH3:13])[C:11]#[N:12])[CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-:17].[K+].[K+].OO>CS(C)=O>[F:15][CH:2]([F:1])[O:3][C:4]1[N:9]=[C:8]([C:10]([CH3:13])([CH3:14])[C:11]([NH2:12])=[O:17])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 67451383HCID 67451383, compound

Product 1

HCID 67452926HCID 67452926, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

To a 1 L round bottom flask was added 2-(6-(difluoromethoxy)pyridin-2-yl)-2-methylpropanenitrile (19.2 g, 91 mmol, 1 equiv), potassium carbonate (37.0 g, 270 mmol, 3 equiv), and DMSO (150 mL). The reaction was cooled to 0° C. and 30% hydrogen peroxide (25 mL) was added slowly in 2 mL portions over ten minutes. The reaction was then warmed to room temperature and stirred for 1 h. After consumption of starting material, the reaction was poured into ethyl acetate (600 mL), washed with brine (3×300 mL), dried over Na2SO4, and concentrated to give 2-(6-(difluoromethoxy)pyridin-2-yl)-2-methylpropanamide (20 g, 97%) as a clear oil.

Workup

  1. temperatureThe reaction was then warmed to room temperature
  2. customAfter consumption of starting material
  3. additionthe reaction was poured into ethyl acetate (600 mL)
  4. washwashed with brine (3×300 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fe21d799837e43969f2217c84f70345c
Source dataset
uspto-grants-2015_04
Patent number
US09018223B2

Reaction notes

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