反応 #2006411

反応方程式

NaHCO3

benzenesulfonyl chloride

3iodoaniline

Et3N

→

title compound 21

収率 94.0%

3-(Benzenesulfonylamino)-phenyl Iodide

収率 94.0%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他a white precipitate was formed
2. 2
   その他the phases were separated
3. 3
   抽出The aqueous layer was extracted several times with CH2Cl2
4. 4
   乾燥the combined extracts were dried over (MgSO4)
5. 5
   その他then 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
   その他The solvent was evaporated under reduced pressure
10. 10
    抽出the aqueous phase was extracted several times with CH2Cl2
11. 11
    乾燥The combined organic extracts were dried over (MgSO4)
12. 12
    その他evaporated
13. 13
    その他The crude material was purified by flash chromatography

実験手順

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.

出典