Reacción #9671

Ecuación de reacción

sulfuryl chloride

Sulfuryl chloride

2-mercapto-5-(trifluoromethyl)benzothiazole

→

2-chloro-5-(trifluoromethyl)benzothiazole

Rendimiento 94.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe product was then extracted with ethyl acetate
2. 2
   LavadoThe organic layer was washed with water (3×) and brine
3. 3
   Secadodried over anhydrous Na2SO4
4. 4
   Concentraciónconcentrated
5. 5
   workup.DISSOLUTIONThe resulting solid was dissolved in EtOAc
6. 6
   Filtraciónfiltered though a short silica-gel column
7. 7
   Lavadoeluting with EtOAc

Procedimiento

Sulfuryl chloride (9.09 g, 67.33 mmol) was added with stirring to 2-mercapto-5-(trifluoromethyl)benzothiazole (2.64 g, 11.22 mmol) over a period of 5 minutes. The reaction mixture was then allowed to stand for approximately 1 h. Ice water was added to the reaction mixture with stirring to decompose the excess of sulfuryl chloride, and the product was then extracted with ethyl acetate. The organic layer was washed with water (3×) and brine, dried over anhydrous Na2SO4 and concentrated. The resulting solid was dissolved in EtOAc and filtered though a short silica-gel column, eluting with EtOAc, to give 2-chloro-5-(trifluoromethyl)benzothiazole (2.50 g, 94%). LC-MS m/z 238.0 (MH+), ret. time 2.55 min; 1H NMR (400 MHz, DMSO-d6) δ 7.81 (d, 1H), 8.38 (m, 2H).

Fuente