Water → 2-t-Butylthio-3-cyano-5-ethylpyridine

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Reaction Steps

t-Butylmercaptan (0.40 mL, 3.55 mmol) was added to a suspension of 60% sodium hydride in mineral oil (158 mg, 3.85 mmol) in dry dimethylformamide (5 mL). After 10 minutes, when gas evolution ceased, 2-chloro-3-cyano-5-ethyl-6-methylpyridine (542 mg, 3.0 mmol) was added. After stirring for one hour, water was added and product extracted into diethyl ether. This extract was dried (Na2SO4), filtered and the solvent removed to give 648 mg (92%) of crystalline product, m.p. 63°-66° C.

Provenance & Evidence