Pyridine → 5,6-Dichloro-2-(2-(trifluoromethoxy)ethoxy)nicotinonitrile

HRID 1020818Notes

Reaction equation

HRID 1020818 reaction equation
[Cl:1][C:2]1[C:3]([Cl:19])=[N:4][C:5]([O:11][CH2:12][CH2:13][O:14][C:15]([F:18])([F:17])[F:16])=[C:6]([CH:10]=1)[C:7]([NH2:9])=O.O=P(Cl)(Cl)Cl.N1C=CC=CC=1>CC#N.[OH-].[Na+]>[Cl:1][C:2]1[C:3]([Cl:19])=[N:4][C:5]([O:11][CH2:12][CH2:13][O:14][C:15]([F:18])([F:16])[F:17])=[C:6]([CH:10]=1)[C:7]#[N:9]

Participants

6

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 86661726HCID 86661726, compound

Product 1

HCID 866617275,6-Dichloro-2-(2-(trifluoromethoxy)ethoxy)nicotinonitrileYield 88.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a mixture of 5,6-dichloro-2-(2-(trifluoromethoxy)ethoxy)nicotinamide (240 mg, 0.75 mmol) in MeCN (10 mL) were added POCl3 (350 mg, 2.3 mmol) and pyridine (360 mg, 4.5 mmol) at room temperature. After being stirred for 2 hours at room temperature, the mixture was diluted with 10 mL of sodium hydroxide solution, then extracted with ethyl acetate (2×50 mL), the combined organic layers were washed with brine twice, dried over Na2SO4 and concentrated to give 5,6-dichloro-2-(2-(trifluoromethoxy)ethoxy)nicotinonitrile (0.20 g, 88%).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washthe combined organic layers were washed with brine twice
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-74797669a8a147078d905539598f2d5a
Source dataset
uspto-grants-2014_05
Patent number
US08716478B2

Reaction notes

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