6-(Trifluoromethyl)-2(3H)-benzothiazolone

Chemical Properties

Synthesis

1217302-63-0

898748-27-1

Ethyl 2-iodophenylcarbamate (1 mmol), cuprous iodide (CuI, 19 mg, 0.1 mmol), and sodium sulfide nonahydrate (Na2S-9H2O, 3 mmol) were added to the Schlenk tube. The reaction tube was evacuated and replaced with argon (repeated 3 times), and then N,N-dimethylformamide (DMF, 2 mL) was added. The reaction mixture was stirred at 80 °C for 10 to 16 hours. Upon completion of the reaction, acetic acid (AcOH, 3 mL) was added to the cooled reaction mixture and the mixture was continued to be stirred at 130°C for 36 hours. At the end of the reaction, saturated sodium bicarbonate solution (10 mL) was added for neutralization, followed by extraction with ethyl acetate. The organic phase was washed sequentially with water, saturated saline and dried with anhydrous sodium sulfate. After the solvent was removed by concentration under reduced pressure, the residue was purified by silica gel column chromatography to afford the target product 6-(trifluoromethyl)benzo[d]thiazol-2(3H)-one.

References