Reaktion #9673

Reaktionsgleichung

2-mercapto-6-(trifluoromethyl)-benzothiazole

Sulfuryl chloride

→

desired product

Ausbeute 91.0%

2-Chloro-6-(trifluoromethyl)benzothiazole

Ausbeute 91.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGwith stirring
2. 2
   SonstigePrecipitation
3. 3
   Sonstigewas formed
4. 4
   workup.STIRRINGstirring
5. 5
   workup.WAITwas continued for 2 h
6. 6
   FiltrationThe solid precipitate was filtered
7. 7
   Waschenrinsed with water
8. 8
   workup.DISSOLUTIONThe wet filter cake was dissolved in 100 mL EtOAc
9. 9
   Waschenthe solution was washed with 100 mL water and 50 mL saturated aqueous NaHCO3 solution
10. 10
    Trocknendried over Na2SO4
11. 11
    SonstigeEtOAc was removed by rotary evaporation
12. 12
    Sonstigethe residue was dried in vacuo

Vorschrift

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).

Quelle