반응 #2006411

반응 방정식

NaHCO3

benzenesulfonyl chloride

3iodoaniline

Et3N

→

title compound 21

수율 94.0%

3-(Benzenesulfonylamino)-phenyl Iodide

수율 94.0%

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타a white precipitate was formed
2. 2
   기타the phases were separated
3. 3
   추출The aqueous layer was extracted several times with CH2Cl2
4. 4
   건조the combined extracts were dried over (MgSO4)
5. 5
   기타then 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
   기타The solvent was evaporated under reduced pressure
10. 10
    추출the aqueous phase was extracted several times with CH2Cl2
11. 11
    건조The combined organic extracts were dried over (MgSO4)
12. 12
    기타evaporated
13. 13
    기타The crude material was purified by flash chromatography

실험 절차

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.

출처