Ethanol → Sodium 3-cyano-1-(2-methylphenyl)-6-oxo-1,6-dihydropyridine-2-thiolate

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Reaction Steps

A solution of sodium bis(trimethylsilyl)amide (84 mL of a 1.0M solution in THF, 84 mmol) was added to a solution of o-tolyl isothiocyanate (5.0 g, 33.5 mmol) and acetonitrile (18 mL, 0.345 mol) in THF (100 mL) at −78° C. The mixture was allowed to warm to r.t. over 3 h. N,N-Dimethyluracil (4.62 g, 33 mmol) and EtOH (75 mL) were added and the mixture heated at reflux for 3 h then stirred at r.t. overnight. Volatiles were removed in vacuo. The residue was used crude in the next step without further purification.

Provenance & Evidence