Sodium hydride → HCID 21464398, compound

HRID 1940925Notes

Reaction equation

HRID 1940925 reaction equation
[Cl:1][C:2]1[C:3]([F:10])=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1F.[O-:11][CH2:12][CH3:13].[Na+].[H-].[Na+]>C(O)C>[Cl:1][C:2]1[C:3]([F:10])=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[O:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2723922Sodium ethoxideHCID 15739314HCID 15739314, compound

Product 1

HCID 21464398HCID 21464398, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a solution of 70.2 g (0.38 mol) of 3,5-dichloro-2,4-difluoropyridine in 600 mL of ethanol was slowly added with stirring a solution of sodium ethoxide in ethanol prepared from 16 g (0.40 mol) of sodium hydride (60 percent in mineral oil, hexane washed) in 200 mL of ethanol. The mixture was allowed to stir overnight and the brown solution obtained was filtered through powdered cellulose and concentrated by evaporation under reduced pressure. The residue was partitioned between 500 mL of ether and 400 mL of water. The organic phase was recovered, dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue was distilled to obtain 62 g (84 percent of theory) of the title compound as a colorless oil having a boiling point of 175°-180° C. at 0.4 mm Hg (53 Pascals).

Workup

  1. customthe brown solution obtained
  2. filtrationwas filtered through powdered cellulose
  3. concentrationconcentrated by evaporation under reduced pressure
  4. customThe residue was partitioned between 500 mL of ether and 400 mL of water
  5. customThe organic phase was recovered
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. distillationThe residue was distilled

Sources & evidence

ORD record
ord-1346a77a99ed4f6fb4d5cfcc2c2318a6
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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