Dimethyl Sulfoxide → 2-((5-Fluoropyridin-3-yl)oxy)acetamide

HRID 56272Notes

Reaction equation

HRID 56272 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][C:10]#[N:11])[CH:5]=[N:6][CH:7]=1.C([O-])([O-])=[O:13].[K+].[K+].CS(C)=O.OO>O>[F:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][C:10]([NH2:11])=[O:13])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 900242292-((5-Fluoropyridin-3-yl)oxy)acetonitrile

Product 1

HCID 900226812-((5-Fluoropyridin-3-yl)oxy)acetamideYield 60.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-((5-fluoropyridin-3-yl)oxy)acetonitrile (0.55 g, 3.62 mmol), K2CO3 (0.60 g, 4.34 mmol) and DMSO (0.55 mL) in H2O (8 mL) was added H2O2 (0.55 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 (0.37 g, 60%).

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-175b413119fa4a558bff252c9f62e0cf
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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