Réaction #1884957

Équation de réaction

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

SnCl2.2H2O

→

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

Rendement 65.0%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was heated
2. 2
   Températureto reflux for 1.5 hr
3. 3
   AutreThe solvent was then removed under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (10 mL)
5. 5
   Lavagewashed with 1N NaOH, water
6. 6
   Séchagedried over MgSO4
7. 7
   AutreEvaporation of the solvent

Mode opératoire

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).

Source