Thionyl Chloride → HCID 20330561, compound

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Reaction Steps

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.

Provenance & Evidence