Water → Phenyl-2-aminoethyl sulfide

Participants

Reaction Steps

Mix 2-aminoethanethiol hydrochloride (4.07 g, 35.6 mmol) in dioxane (75 mL) at 50° C. Add sodium hydride (60% in mineral oil, 2.84 g, 71.0 mmol) at room temperature under nitrogen. Stir the reaction for 5 minutes. Add 2-chloropyridine (3.5 mL, 37 mmol) to the mixture. Reflux the mixture for 24 hours, and then cool to room temperature. Add water (100 mL), and methylene chloride (300 mL) to this mixture. Extract the aqueous layer with methylene chloride (3×50 mL). Wash the combined organic phase with brine (200 mL), dry (magnesium sulfate), filter and concentrate to an orange oil. Perform flash chromatography on silica gel eluting with 50% (80:18:12 CHCl3/MeOH/concentrated NH4OH)/methylene chloride to afford the title compound as a yellow oil (1.67 g) m/e=155 (MH+).

Provenance & Evidence