반응 #1884957

ord-64be9c6243234337a7e70793f4f6778c

반응 방정식

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
수율 65.0%

용매

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도The reaction mixture was heated
  2. 2
    온도to reflux for 1.5 hr
  3. 3
    기타The solvent was then removed under reduced pressure
  4. 4
    workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (10 mL)
  5. 5
    세척washed with 1N NaOH, water
  6. 6
    건조dried over MgSO4
  7. 7
    기타Evaporation of the solvent

실험 절차

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).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08343457B2uspto-grants-2013_01