Реакция #2006411

Уравнение реакции

NaHCO3

benzenesulfonyl chloride

3iodoaniline

Et3N

→

title compound 21

Выход 94.0%

3-(Benzenesulfonylamino)-phenyl Iodide

Выход 94.0%

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   Другоеa white precipitate was formed
2. 2
   Другоеthe phases were separated
3. 3
   ЭкстракцияThe aqueous layer was extracted several times with CH2Cl2
4. 4
   Сушкаthe combined extracts were dried over (MgSO4)
5. 5
   Другоеthen 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
   ДругоеThe solvent was evaporated under reduced pressure
10. 10
    Экстракцияthe aqueous phase was extracted several times with CH2Cl2
11. 11
    СушкаThe combined organic extracts were dried over (MgSO4)
12. 12
    Другоеevaporated
13. 13
    ДругоеThe crude material was purified by flash chromatography

Методика

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.

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