Reaction #9670

Reaction equation

carbon disulfide

sodium hydride

diethylene glycol monoethyl ether

2-chloro-5-(trifluoromethyl)aniline

→

2-mercapto-5-(trifluoromethyl)benzothiazole

Yield 44.1%

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was then heated at 140° C. for 6 hours
2. 2
   TemperatureAfter cooling the solution to rt
3. 3
   Otherthe product was precipitated by addition of conc. HCl
4. 4
   Filtrationcollected by filtration
5. 5
   Otherrecrystallized from isopropyl ether

Procedure

To a mixture of sodium hydride (0.98 g, 40.91 mmol) and diethylene glycol monoethyl ether (25 mL) was added 2-chloro-5-(trifluoromethyl)aniline (5.00 g, 25.57 mmol) under a nitrogen atmosphere. The resulting mixture was stirred at rt for 30 minutes, and then carbon disulfide (3.89 g, 51.13 mmol) was added. The reaction mixture was then heated at 140° C. for 6 hours. After cooling the solution to rt, the product was precipitated by addition of conc. HCl, collected by filtration, and recrystallized from isopropyl ether to afford 2-mercapto-5-(trifluoromethyl)benzothiazole (2.65 g, 44%). 1H NMR (400 MHz, DMSO-d6) δ 7.49 (s, 1H), 7.61 (d, 1H), 7.94 (d, 1H).

Source