Sodium Hydroxide → 2-({[3-(Trifluoromethyl)phenyl]sulfanyl}methyl)pyridine--hydrogen chloride (1/1)

Participants

Reaction Steps

m-Trifluoromethylbenzenethiol (5 g) was added to a solution of NaOH (2.25 g) in ethanol (50 ml) and the resulting solution was treated with a solution of 2-picolyl chloride, hydrochloride (4.6 g) in ethanol (25 ml) and the mixture was stirred for 5 hours. The resulting suspension was filtered through kieselghur and the solvent was removed by evaporation. The residue was converted into the hydrochloride in ether with ethereal HCl and recrystallised from acetone-ether to give 2-(((3-trifluoromethylphenyl)thio)methyl)pyridine hydrochloride (4.8 g) mp 145°-6° C. (Found: C,51.1; H,4.0; N,4.7 C13H10F3NS.HCl requires C,51.0; H,3.6; N,4.6%).

Provenance & Evidence