反应详情

To a solution of 4-(4-aminophenyl)butyric acid (1 g, 5.6 mmol) in dry acetone (30 ml) was added dropwise a solution of benzenesulphonyl chloride (0.99 g) and pyridine (1.1 g) in dry acetone (10 ml). The mixture was heated at reflux for 3 hours, then concentrated in vacuo. The resulting oil was dissolved in dichloromethane (100 ml) and the solution was washed with 2N aqueous HCl (2×100 ml), followed by water (2×100 ml). The dichloromethane solution was extracted with 10% aqueous NaOH (2×50 ml), followed by water (2×50 ml), and these extracts were combined and stirred with dichloromethane (100 ml) while conc. HCl was added to adjust the pH of the mixture to 5. The layers were separated and the organic solution was dried (MgSO04) and concentrated in vacuo. The resulting solid was recrystallised from isopropanol to give 4-[4-(phenyl-sulphonamido)phenyl]butyric acid. (1.03 g, 58%) mp. 128°-130 ° C.

1. temperatureThe mixture was heated
2. temperatureat reflux for 3 hours
3. concentrationconcentrated in vacuo
4. dissolutionThe resulting oil was dissolved in dichloromethane (100 ml)
5. washthe solution was washed with 2N aqueous HCl (2×100 ml)
6. extractionThe dichloromethane solution was extracted with 10% aqueous NaOH (2×50 ml)
7. additionwas added
8. customThe layers were separated
9. customthe organic solution was dried (MgSO04)
10. concentrationconcentrated in vacuo
11. customThe resulting solid was recrystallised from isopropanol