Reaction #1772013

Reaction equation

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

SnCl2.2H2O

→

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

Yield 65.0%

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was heated
2. 2
   Temperatureto reflux for 1.5 hr
3. 3
   OtherThe solvent was then removed under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (10 mL)
5. 5
   Washwashed with 1N NaOH, water
6. 6
   Dryingdried over MgSO4
7. 7
   OtherEvaporation of the solvent

Procedure

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