Trifluoroacetic anhydride → 6-Chloro-1-oxo-1lambda~5~-pyridine-3-carbonitrile

HRID 1791902Notes

Reaction equation

HRID 1791902 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.OO.NC(N)=[O:14].FC(F)(F)C(OC(=O)C(F)(F)F)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N+:3]=1[O-:14]

Participants

6

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 24477Sodium ThiosulfateHCID 31294Carbamide PeroxideHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 220285946-Chloro-1-oxo-1lambda~5~-pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloropyridine-5-carbonitrile (7.01 g) was dissolved in acetonitrile (70 mL), and urea hydrogen peroxide addition compound (10 g) was added. Trifluoroacetic anhydride was added dropwise to the reaction mixture under ice-cooling and the mixture was stirred at room temperature for 18 hr. The reaction mixture was added to aqueous sodium thiosulfate solution and the mixture was extracted with chloroform. The extract was washed successively with saturated aqueous sodium hydrogencarbonate solution and brine and dried. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography to give 2-chloro-5-cyanopyridine 1-oxide (0.779 g) as a white solid.

Workup

  1. additionwas added
  2. temperaturecooling
  3. extractionthe mixture was extracted with chloroform
  4. washThe extract was washed successively with saturated aqueous sodium hydrogencarbonate solution and brine
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-999a2d1f33744c50bceba70860d4b33a
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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