Hydrogen Peroxide → HCID 66669143, compound

HRID 512055Notes

Reaction equation

HRID 512055 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:13]=[N:14][C:15]([O:19][CH3:20])=[C:16]([Cl:18])[CH:17]=1)[C:5]#[N:6].C(=O)([O-])[O-:22].[K+].[K+].OO>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:13]=[N:14][C:15]([O:19][CH3:20])=[C:16]([Cl:18])[CH:17]=1)[C:5]([NH2:6])=[O:22]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 66666899HCID 66666899, compound

Product 1

HCID 66669143HCID 66669143, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of 3-chloro-4-[(5-chloro-6-methoxypyridin-3-yl)methoxy]benzonitrile (Preparation 30, 64 mg, 0.21 mmol) and potassium carbonate (57 mg, 0.414 mmol) in DMSO (5 mL) was added hydrogen peroxide (141 mL, 4.14 mmol) and the reaction stirred at room temperature for 1 hour. The reaction was quenched with water (10 mL) and extracted with EtOAc (10 mL). The organic layer was washed with water (2×10 mL), dried over sodium sulfate and concentrated in vacuo to afford a white solid, which was triturated with EtOAc to yield the title compound (30 mg, 44%).

Workup

  1. customThe reaction was quenched with water (10 mL)
  2. extractionextracted with EtOAc (10 mL)
  3. washThe organic layer was washed with water (2×10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford a white solid, which
  7. customwas triturated with EtOAc

Sources & evidence

ORD record
ord-c697d8b526454dc7957550917d23fd59
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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