Reacción #2006411

Ecuación de reacción

NaHCO3

benzenesulfonyl chloride

3iodoaniline

Et3N

→

title compound 21

Rendimiento 94.0%

3-(Benzenesulfonylamino)-phenyl Iodide

Rendimiento 94.0%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroa white precipitate was formed
2. 2
   Otrothe phases were separated
3. 3
   ExtracciónThe aqueous layer was extracted several times with CH2Cl2
4. 4
   Secadothe combined extracts were dried over (MgSO4)
5. 5
   Otrothen evaporated
6. 6
   workup.DISSOLUTIONThe crude mixture was dissolved in MeOH (100 mL)
7. 7
   workup.ADDITIONNaOMe (6 g), was added
8. 8
   workup.ADDITIONwas added
9. 9
   OtroThe solvent was evaporated under reduced pressure
10. 10
    Extracciónthe aqueous phase was extracted several times with CH2Cl2
11. 11
    SecadoThe combined organic extracts were dried over (MgSO4)
12. 12
    Otroevaporated
13. 13
    OtroThe crude material was purified by flash chromatography

Procedimiento

To a solution of 3iodoaniline (5 g, 22.8 mmol), in CH2Cl2 (100 mL), were added at room temperature Et3N (6.97 mL) followed by benzenesulfonyl chloride (5.84 mL). The mixture was stirred 4 h then a white precipitate was formed. A saturated aqueous solution of NaHCO3 was added and the phases were separated. The aqueous layer was extracted several times with CH2Cl2 and the combined extracts were dried over (MgSO4) then evaporated. The crude mixture was dissolved in MeOH (100 mL) and NaOMe (6 g), was added and the mixture was heated 1 h at 60° C. The solution became clear with time and HCl (1N) was added. The solvent was evaporated under reduced pressure then the aqueous phase was extracted several times with CH2Cl2. The combined organic extracts were dried over (MgSO4) and evaporated. The crude material was purified by flash chromatography using (100% CH2Cl2) as solvent yielding the title compound 21 (7.68g, 94%) as yellow solid.

Fuente