Nicotinic Acid → 2-(3-Pyridyl)benzothiazole

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Reaction Steps

o-Aminothiophenol 36.9 g (0.30 mole) and nicotinic acid 55.5 g (0.45 mole) are dissolved in 600 cc of chloroform and 360 g of polyphosphoric acid ethyl ester (PPE). The resulting solution is heated at reflux for 1 hour. It is then concentrated to dryness. The residue is poured onto 1500 cc of ice-water, and the resulting mixture is brought to pH 10 with 50% NaOH solution. The aqueous mixture is extracted with CHCl3, and the extracts dried (MgSO4), filtered, and concentrated in vacuo. The residue is recrystallized from acetonitrile to yield the title A compound (42.8 g, 68%, of theory).

Provenance & Evidence