Water → 2-(3-chloro-2-oxo-5-(trifluoromethyl)pyridin-1(2H)-yl)acetonitrile

HRID 2106794Notes

Reaction equation

HRID 2106794 reaction equation
[Cl:1][C:2]1[C:3]([OH:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Br[CH2:14][C:15]#[N:16].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[C:15]([CH2:14][N:4]1[CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=[C:2]([Cl:1])[C:3]1=[O:12])#[N:16]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 7254363-Chloro-5-(trifluoromethyl)pyridin-2-ol

Product 1

HCID 148369742-(3-chloro-2-oxo-5-(trifluoromethyl)pyridin-1(2H)-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4.0 g (0.02 mole) of 3-chloro-5-(trifluoromethyl)-2-pyridinol, 2.6 g (0.022 mole) of monobromoacetonitrile, and 4.0 g of potassium carbonate in 40 ml of dimethyl sulfoxide was prepared and stirred at ambient temperature for 3 hours. Water was then added and the light brown solid that formed was separated by filtration and dried to obtain 2.3 g (45 percent of theory) of the title compound: melting point, 84°-85° C. This product had infrared and nmr spectra compatible with the assigned structure.

Workup

  1. customwas prepared
  2. customthe light brown solid that formed
  3. customwas separated by filtration
  4. customdried

Sources & evidence

ORD record
ord-af70d62b02b849e6902faf4a7abfc074
Source dataset
uspto-grants-1990_06
Patent number
US04931452

Reaction notes

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