Sodium Chloride → HCID 21486886, compound

HRID 1659124Notes

Reaction equation

HRID 1659124 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-2367d074188b4f688ec541262bf4e7de
Source dataset
uspto-grants-1976_06
Patent number
US03966945

Reaction notes

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