Water → HCID 178425677, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of sodium hydrosulphide hydrate (22.0 g) in ethylene glycol (100 ml) at 100° C. was added 2-bromo-6-(4-toluoyl)pyridine (27.6 g) in portions. The mixture was then heated at 110° C. for 3 hours, allowed to cool and then poured into water (600 ml). The yellow precipitate of the by-product 6-(4-methylbenzyl)pyridine-2-thiol was filtered off and the filtrate was acidified by the addition of glacial acetic acid (10 ml). The resultant orange solid was then filtered off and well washed with water and dried. This crude solid (19.4 g) was crystallised from a mixture of benzene (500 ml) and methanol (175 ml) to give 6-(4-toluoyl)pyridine-2-thiol (10.0 g) as orange needles. M.p. 179°-181°.

Provenance & Evidence