Reacción #9673

Ecuación de reacción

2-mercapto-6-(trifluoromethyl)-benzothiazole

Sulfuryl chloride

→

desired product

Rendimiento 91.0%

2-Chloro-6-(trifluoromethyl)benzothiazole

Rendimiento 91.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGwith stirring
2. 2
   OtroPrecipitation
3. 3
   Otrowas formed
4. 4
   workup.STIRRINGstirring
5. 5
   workup.WAITwas continued for 2 h
6. 6
   FiltraciónThe solid precipitate was filtered
7. 7
   Lavadorinsed with water
8. 8
   workup.DISSOLUTIONThe wet filter cake was dissolved in 100 mL EtOAc
9. 9
   Lavadothe solution was washed with 100 mL water and 50 mL saturated aqueous NaHCO3 solution
10. 10
    Secadodried over Na2SO4
11. 11
    OtroEtOAc was removed by rotary evaporation
12. 12
    Otrothe residue was dried in vacuo

Procedimiento

Sulfuryl chloride (40 mL) was added with stirring to 2-mercapto-6-(trifluoromethyl)-benzothiazole (18.0 g, 76.7 mmol) at <20° C. under a nitrogen atmosphere, and the suspension was then stirred at rt for 2 h. The reaction mixture was poured into ice water with stirring. Precipitation was formed, and stirring was continued for 2 h. The solid precipitate was filtered, and rinsed with water. The wet filter cake was dissolved in 100 mL EtOAc, and the solution was washed with 100 mL water and 50 mL saturated aqueous NaHCO3 solution, then dried over Na2SO4. EtOAc was removed by rotary evaporation, and the residue was dried in vacuo to afford the desired product as a light yellow solid (16.5 g, 91%). GC-EIMS m/z 237 (M+); 1H NMR (CDCl3) δ 8.10 (s, 1 H), 8.00 (d, 1 H), 7.70 (d, 1 H).

Fuente