p-Chlorothiophenol → 2-{[(4-Chlorophenyl)sulfanyl]methyl}pyridine--hydrogen chloride (1/1)

Participants

Reaction Steps

4-Chlorobenzenethiol (5 g) in warm ethanol (5 ml) was added to a solution of sodium hydroxide (2.8 g) in ethanol (50 ml). To the solution was added a solution of 2-picolyl chloride, hydrochloride (5.7 g) in ethanol (25 ml) and the mixture was stirred at ambient temperature for 6 hours. The mixture was filtered and evaporated and the residue was converted into the hydrochloride with ethereal HCl solution and this was recrystallised from ethanol-ether to give 2-(((4-chlorophenyl)thio)methyl)pyridine, hydrochloride (8 g) mp 196°-8° C. (Found: C, 52.95; H, 4.1; N, 5.15. C12H10ClNS.HCl requires C, 53.1; H, 4.2; N, 4.9%).

Provenance & Evidence