Hydrogen Peroxide → HCID 66666483, compound

HRID 1620334Notes

Reaction equation

HRID 1620334 reaction equation
OO.[CH3:3][O:4][C:5]1[C:10]([C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=2[O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]#[N:15])=[CH:9][CH:8]=[CH:7][N:6]=1.C(=O)([O-])[O-:27].[K+].[K+]>CS(C)=O>[CH3:3][O:4][C:5]1[C:10]([C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=2[O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]([NH2:15])=[O:27])=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 66666740HCID 66666740, compound

Product 1

HCID 66666483HCID 66666483, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 30% aqueous hydrogen peroxide (1 mL, 7.6 mmol) was added dropwise to a suspension of 3-(2-methoxypyridin-3-yl)-4-phenoxybenzonitrile (Preparation 20, 0.23 g, 0.76 mmol) and potassium carbonate (0.64 g, 4.6 mmol) in DMSO (3 mL). The reaction mixture was stirred for 2 hours at room temperature, then quenched with aqueous sodium thiosulfate solution (10% w/v, 10 mL) and extracted with EtOAc (50 mL). The organic layer was dried over sodium sulfate and the solvent removed in vacuo to afford the title compound as a pale yellow solid (0.2 g).

Workup

  1. customquenched with aqueous sodium thiosulfate solution (10% w/v, 10 mL)
  2. extractionextracted with EtOAc (50 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-12fdf26bda4a4eb5bd3ddb5c51aa0570
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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