Reacción #1884957

Ecuación de reacción

2-(4′-nitrophenyl)-6-methylsulfoxy benzothiazole

SnCl2.2H2O

→

2-(4′-aminophenyl)-6-methylsulfoxy benzothiazole

Rendimiento 65.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was heated
2. 2
   Temperaturato reflux for 1.5 hr
3. 3
   OtroThe solvent was then removed under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (10 mL)
5. 5
   Lavadowashed with 1N NaOH, water
6. 6
   Secadodried over MgSO4
7. 7
   OtroEvaporation of the solvent

Procedimiento

To a solution of 2-(4′-nitrophenyl)-6-methylsulfoxy benzothiazole (35 mg, 0.10 mmol) dissolved in ethanol (10 mL) was added SnCl2.2H2O (50 mg). The reaction mixture was heated to reflux for 1.5 hr. The solvent was then removed under reduced pressure. The residue was dissolved in ethyl acetate (10 mL), washed with 1N NaOH, water, dried over MgSO4. Evaporation of the solvent afforded 2-(4′-aminophenyl)-6-methylsulfoxy benzothiazole (21 mg, 65%) as pale brown solid. 1HNMR (300 MHz, CDCl3) δ (ppm): 8.02(d, J=6.2 Hz, 1H), 7.92(d, J=8.7 Hz, 2H), 7.84(d, J=2.4 Hz, 1H), 7.38(dd, J1=2.4 Hz, J2=6.2 Hz, 1H), 6.78(d, J=8.7 Hz, 2H), 2.21(s, 3H, CH3).

Fuente