75-15-0

29289-13-2

2268-79-3

2-Iodo-4-methylaniline (2 mmol), carbon disulfide (10 mmol), sodium sulfide (4 mmol), and N,N-dimethylformamide (2 mL) were added to a 50 mL sealed tube at room temperature and protected by argon and sealed by three times of argon displacement. The reaction mixture was stirred electromagnetically at 110 °C for 12 h. The reaction progress was monitored by thin layer chromatography (TLC) on silica gel plates. After completion of the reaction, the mixture was cooled to room temperature, 3 mol/L hydrochloric acid (2 mL) was added and stirred for 30 min. Subsequently, the reaction mixture was extracted with dichloromethane (3 x 20 mL). The organic phases were combined, dried with anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography with the eluent being a mixed petroleum ether/ethyl acetate solvent to afford the target product 6-methylbenzo[d]thiazole-2-thiol.