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2-Bromopyridine reacts with butyllithium to give 2-lithiopyridine, [2] which is a versatile reagent. [3] Pyrithione can be prepared in a two-step synthesis from 2-bromopyridine by oxidation to the N-oxide with a suitable peracid followed by substitution using either sodium dithionite or sodium sulfide with sodium hydroxide to introduce the thiol functional group.
Pyrithione is the common name of an organosulfur compound with molecular formula C 5 H 5 NOS, chosen as an abbreviation of pyridinethione, and found in the Persian shallot. [4] It exists as a pair of tautomers, the major form being the thione 1-hydroxy-2(1H)-pyridinethione and the minor form being the thiol 2-mercaptopyridine N-oxide; it crystallises in the thione form. [5]
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2-Mercaptopyridine was originally synthesized in 1931 by heating 2-chloropyridine with calcium hydrogen sulfide. [2]ClC 5 H 4 N + Ca(SH) 2 → HSC 5 H 4 N + Ca(SH)Cl. A more convenient route to 2-mercaptopyridine is the reaction of 2-chloropyridine and thiourea in ethanol and aqueous ammonia.