Ammonium Hydroxide → 4-Trifluoromethyl-thiazole-2-carboxylic acid amide

Participants

Reaction Steps

To a solution of 4-trifluoromethyl-thiazole-2-carboxylic acid (50 g, 1 eq.) in anhydrous THF (480 mL) was added carbodiimidazole (45.2 g, 1.1 eq.) portionwise under nitrogen in an ice/water bath (about 5° C.). The reaction mixture was stirred at room temperature for 16 hrs. NH4OH (25% in H2O; 1.930 mL) was added. The solution was stirred for 4 hrs, and then partitioned in DCM (500 mL) and H2O (500 mL). Aqueous layer was further extracted with DCM (500 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to yield compound 285a as an orange solid in 72% yield. MS (ESI, EI+) m/z=197 (MH+).

Provenance & Evidence