反応 #1772013

ord-7feeedf927c249cfbfd5096ba8896167

反応方程式

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
収率 65.0%

溶媒

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

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

実験手順

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).

出典

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