Dimethyl Sulfoxide → 2-(Pyridin-3-yloxy)acetamide

HRID 56269Notes

Reaction equation

HRID 56269 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][C:9]#[N:10])[CH:2]=1.C([O-])([O-])=[O:12].[K+].[K+].CS(C)=O.OO>O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][C:9]([NH2:10])=[O:12])[CH:2]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 199146182-(Pyridin-3-yloxy)acetonitrile

Product 1

HCID 183478302-(Pyridin-3-yloxy)acetamideYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-(pyridin-3-yloxy)acetonitrile (100 mg, 0.75 mmol), K2CO3 (103 mg, 0.75 mmol) and DMSO (0.1 mL) in H2O (2 mL) was added H2O2 (0.1 mL, 30%) dropwise in an ice bath and the mixture was stirred at rt for 5 min. It was then concentrated in vacuo and the residue was purified by a silica gel column chromatography (EtOAc) to give the title compound as a white solid (62.2 mg, 55%).

Workup

  1. concentrationIt was then concentrated in vacuo
  2. customthe residue was purified by a silica gel column chromatography (EtOAc)

Sources & evidence

ORD record
ord-790dda0b2cec4f10aeb361507685b63b
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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