Thionyl Chloride → HCID 20330561, compound

HRID 2057791Notes

Reaction equation

HRID 2057791 reaction equation
S(Cl)(Cl)=O.[O:5]([C:12]1[CH:13]=[CH:14][C:15]([CH:18]=[N:19]O)=[N:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[O:5]([C:12]1[CH:13]=[CH:14][C:15]([C:18]#[N:19])=[N:16][CH:17]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 136335624HCID 136335624, compound

Product 1

HCID 20330561HCID 20330561, compound

Procedure

A solution of sodium amide is prepared using 5 g of sodium metal in 500 ml liquid ammonia and 0.1 g ferric nitrate catalyst. A solution of 19 g of 2-methyl-5-phenoxypyridine in 20 ml of anhydrous diethylether is added dropwise, followed by a solution of 11 g of n-butylnitrite in 20 ml of anhydrous diethylether. The ammonia is allowed to evaporate and the resulting mixture of solids is treated with 27 g of ammonium sulfate, 100 ml of diethylether and 100 ml of water. The mixture is extracted with 500 ml of dichloromethane. The organic solution is dried, concentrated and the mixture of oximes can be used directly. One isomer is isolated by crystallization from anhydrous diethylether, 5-phenoxy-2-pyridinecarboxaldehyde oxime, m.p. 130°-131° C. To 59 g of reagent thionylchloride is added 5 g of 5-phenoxy-2-pyridinecarboxaldehyde oxime in portions. After the initial exothermic reaction subsides, the solution is refluxed 30 minutes. The solution is concentrated at reduced pressure, is dissolved in 200 ml dichloromethane and is washed until neutral with dilute ammonium hydroxide. The organic solution is dried, concentrated and distilled to yield 5-phenoxy-2-pyridinecarbonitrile, m.p. 84°-85° C., identical by mixed melting point, infrared and proton magnetic resonance spectrum to that prepared by Process I.

Workup

  1. customAfter the initial exothermic reaction subsides
  2. temperaturethe solution is refluxed 30 minutes
  3. concentrationThe solution is concentrated at reduced pressure
  4. dissolutionis dissolved in 200 ml dichloromethane
  5. washis washed until neutral with dilute ammonium hydroxide
  6. customThe organic solution is dried
  7. concentrationconcentrated
  8. distillationdistilled

Sources & evidence

ORD record
ord-8b93ae1274cd4f52badcff21ef1f3d0a
Source dataset
uspto-grants-1980_07
Patent number
US04212980

Reaction notes

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