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3. Ex (SOCl2)

Amide to Nitrile

(SOCl₂)

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Examples:

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Example 1

A suspension of the SM (10 g, 78 mmol) in SOCl2 (35 mL) was refluxed for 4 h until the suspension became homogenous. The reaction mixture was then cooled to RT and poured onto 300 g of crushed ice. The ice slurry melted and was treated with KOH pellets until pH 9. The mixture was concentrated to a residue and partitioned between H2O and CHCl3. The layers were separated and the aq layer was further extracted with CHCl3 (4x). The combined organics were concentrated to provide the product as a brown oil. [3.1 g, 36%]

[Patent Reference: WO2010104899, page 155, (6.7 MB)]