Reaction #2006411

Reaction equation

NaHCO3

benzenesulfonyl chloride

3iodoaniline

Et3N

→

title compound 21

Yield 94.0%

3-(Benzenesulfonylamino)-phenyl Iodide

Yield 94.0%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Othera white precipitate was formed
2. 2
   Otherthe phases were separated
3. 3
   ExtractionThe aqueous layer was extracted several times with CH2Cl2
4. 4
   Dryingthe combined extracts were dried over (MgSO4)
5. 5
   Otherthen 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
   OtherThe solvent was evaporated under reduced pressure
10. 10
    Extractionthe aqueous phase was extracted several times with CH2Cl2
11. 11
    DryingThe combined organic extracts were dried over (MgSO4)
12. 12
    Otherevaporated
13. 13
    OtherThe crude material was purified by flash chromatography

Procedure

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