Réaction #2006411

Équation de réaction

NaHCO3

benzenesulfonyl chloride

3iodoaniline

Et3N

→

title compound 21

Rendement 94.0%

3-(Benzenesulfonylamino)-phenyl Iodide

Rendement 94.0%

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Autrea white precipitate was formed
2. 2
   Autrethe phases were separated
3. 3
   ExtractionThe aqueous layer was extracted several times with CH2Cl2
4. 4
   Séchagethe combined extracts were dried over (MgSO4)
5. 5
   Autrethen 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
   AutreThe solvent was evaporated under reduced pressure
10. 10
    Extractionthe aqueous phase was extracted several times with CH2Cl2
11. 11
    SéchageThe combined organic extracts were dried over (MgSO4)
12. 12
    Autreevaporated
13. 13
    AutreThe crude material was purified by flash chromatography

Mode opératoire

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.

Source