Pyridine-2-carbonitrile → 2-(2-pyridyl)-4H-1,3-benzothiazin-4-one

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Reaction Steps

Methyl thiosalicylate (1.6 g, 9.51 mM) and 2-cyanopyridine (1.0 g, 9.60 mM) were dissolved in toluene (2 ml), and triethylamine (2 ml, 14.4 mM) was added to the solution. After heating for 8 hours under reflux, toluene was removed by distillation. Ethanol was added to the residue and the precipitates were taken out by filtration to give crude crystals (1.7 g). The crude crystals were purified by silica gel column chromatography (hexane:chloroform=5:1→chloroform) to give the title compound as crystals (1.0 g, 43.4%).

Provenance & Evidence