反应 #1772013

ord-7feeedf927c249cfbfd5096ba8896167

反应方程式

Cc1cc(OS(=O)(=O)O)c2nc(-c3ccc([N+](=O)[O-])cc3)sc2c1
2-(4′-nitrophenyl)-6-methylsulfoxy benzothiazole
O.O.[Cl][Sn][Cl]
SnCl2.2H2O
Cc1cc(OS(=O)(=O)O)c2nc(-c3ccc(N)cc3)sc2c1
2-(4′-aminophenyl)-6-methylsulfoxy benzothiazole
收率 65.0%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    温度The reaction mixture was heated
  2. 2
    温度to reflux for 1.5 hr
  3. 3
    其他The solvent was then removed under reduced pressure
  4. 4
    workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (10 mL)
  5. 5
    洗涤washed with 1N NaOH, water
  6. 6
    干燥dried over MgSO4
  7. 7
    其他Evaporation of the solvent

实验过程

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).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08147798B2uspto-grants-2012_04