Реакция #9673

Уравнение реакции

2-mercapto-6-(trifluoromethyl)-benzothiazole

Sulfuryl chloride

→

desired product

Выход 91.0%

2-Chloro-6-(trifluoromethyl)benzothiazole

Выход 91.0%

Условия реакции

Обработка

1. 1
   workup.STIRRINGwith stirring
2. 2
   ДругоеPrecipitation
3. 3
   Другоеwas formed
4. 4
   workup.STIRRINGstirring
5. 5
   workup.WAITwas continued for 2 h
6. 6
   ФильтрацияThe solid precipitate was filtered
7. 7
   Промывкаrinsed with water
8. 8
   workup.DISSOLUTIONThe wet filter cake was dissolved in 100 mL EtOAc
9. 9
   Промывкаthe solution was washed with 100 mL water and 50 mL saturated aqueous NaHCO3 solution
10. 10
    Сушкаdried over Na2SO4
11. 11
    ДругоеEtOAc was removed by rotary evaporation
12. 12
    Другоеthe residue was dried in vacuo

Методика

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).

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