Process for the manufacture of 2-mercapto pyridine-1-oxides

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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2602948T, 260295AM, 260296R, 260270K, C07D21389

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active

040803295

ABSTRACT:
A process for the manufacture of 2-mercaptopyridine-1-oxides and zinc salts thereof, comprising the steps of oxidizing a 2-acetylaminopyridine with peracetic acid in an inert solvent to give a 2-acetamidopyridine-1-oxide, cleaving the acetyl group with mineral acid to give a 2-aminopyridine-1-oxide, diazotizing the 2-aminopyridine-1-oxide and treating the diazonium salt with hydrochloric acid to give a 2-chloropyridine-1-oxide, treating the latter with a sulfhydryl-donor to give a 2-mercaptopyridine-1-oxide, and optionally treating the latter with a zinc salt to make the 2:1 zinc salt of the 2-mercaptopyridine-1-oxide. The resulting zinc salts are useful in anti-dandruff preparations.

REFERENCES:
patent: 3249597 (1966-05-01), Dehn et al.
Adams et al. J. Am. Chem. Soc. vol. 76 (10) May 20, 1954.
Abramovitch, Pyridine and its Derivatives, Supplement Part Two, Wiley Pub. pp. 221-225 (1974).
Klingsberg Pyridine and its Derivatives, Part Two Interscience Pub. (1961).
Ochiai, J. Org. Chem. vol. 18, pp. 534-542 (1953).
Fieser & Fieser, Advanced Organic Chemistry, Reinhold Pub. pp. 634-635 (1961).

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