Hydrogen Sulfide → 2-{4-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl}-1,3-thiazole-5-carbothioamide

Participants

Reaction Steps

To a solution of 2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3-thiazole-5-carbonitrile (354 mg, 1.0 mmol) in dioxane was added Et3N (20 μL, 0.14 mmol) and H2S (gas) was bubbled through the solution for about 1 min. After stirring at room temperature for 3 h, ethanol was added, followed by 21 wt. % NaOEt in ethanol (238 μL, 0.6 mmol). More H2S (gas) was bubbled through the solution for another minute. The mixture was then stirred at room temperature for 3 days. Volatile materials were removed in vacuo. The residue was dissolved in EtOAc, washed twice with water, dried (Na2SO4) and concentrated. Trituration with Et2O gave the title compound as a pale yellow solid.

Provenance & Evidence