Sodium Chloride → HCID 21486886, compound

HRID 1604890Notes

Reaction equation

HRID 1604890 reaction equation
[Cl-].[Na+].[CH3:3][O:4][CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[C:6]([NH2:8])=O.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>ClCCCl>[CH3:3][O:4][CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[C:6]#[N:8]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 21486876HCID 21486876, compound

Product 1

HCID 21486886HCID 21486886, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To 20 ml. of dry 1,2-dichloroethane containing 2.0 g. of sodium chloride is added 3.32 g. of 2-methoxy-2-(2-pyridyl)acetamide. After stirring at room temperature for 15 minutes, 1.7 ml. of phosphorus oxychloride is added. The solution is refluxed for 18 hours. The solution is then cooled and made basic with 10% aqueous sodium hydroxide solution. The aqueous phase is extracted three times with chloroform and the combined chloroform extracts are washed three times with water and once with brine and dried over magnesium sulfate. Filtration, removal of solvent and distillation in vacuo gives 2-methoxy-2-(2-pyridyl)acetonitrile, b.p. 72°-76°C./0.2 mm.

Workup

  1. temperatureThe solution is refluxed for 18 hours
  2. temperatureThe solution is then cooled
  3. extractionThe aqueous phase is extracted three times with chloroform
  4. washthe combined chloroform extracts are washed three times with water
  5. dry with materialonce with brine and dried over magnesium sulfate
  6. filtrationFiltration, removal of solvent and distillation in vacuo

Sources & evidence

ORD record
ord-3a4ebe1502d247ed9bee7498a46bae7f
Source dataset
uspto-grants-1976_04
Patent number
US03948892

Reaction notes

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