반응 #46130

반응 방정식

2-amino-5-methoxybenzenesulphonamide

(1-ethoxycyclopropyloxy)trimethylsilane

acetic acid

→

expected compound

2-cyclopropylamino-5-methoxybenzenesulphonamide

용매

methanol

water

반응 조건

후처리

1. 1
   온도heating
2. 2
   온도at reflux
3. 3
   기타The mixture is then evaporated to dryness under reduced pressure
4. 4
   기타The oil obtained
5. 5
   추출extracted with chloroform (3×30 mL)
6. 6
   기타The organic phases are collected
7. 7
   건조dried over anhydrous MgSO4
8. 8
   여과After filtration
9. 9
   기타the filtrate is evaporated to dryness
10. 10
    workup.DISSOLUTIONthe residual oil is dissolved in THF (50 mL)
11. 11
    workup.ADDITIONSodium borohydride (2 g) and boron trifluoride etherate (2 mL) are added
12. 12
    온도the mixture is heated
13. 13
    온도at reflux for 18 hours
14. 14
    기타The solvent is then removed by evaporation under reduced pressure
15. 15
    workup.ADDITIONby adding 6N HCl
16. 16
    추출extracted with chloroform (3×30 mL)
17. 17
    기타The organic phases are collected
18. 18
    건조dried over anhydrous MgSO4
19. 19
    여과After filtration
20. 20
    기타the filtrate is evaporated to dryness

실험 절차

To a solution of 2-amino-5-methoxybenzenesulphonamide (4.9 mmol) in methanol (20 mL) there are added (1-ethoxycyclopropyloxy)trimethylsilane (4 mL) and glacial acetic acid (4 mL) and then heating at reflux is carried out for 18 hours. The mixture is then evaporated to dryness under reduced pressure. The oil obtained is taken up in water (30 mL) and extracted with chloroform (3×30 mL). The organic phases are collected and dried over anhydrous MgSO4. After filtration, the filtrate is evaporated to dryness and the residual oil is dissolved in THF (50 mL). Sodium borohydride (2 g) and boron trifluoride etherate (2 mL) are added and then the mixture is heated at reflux for 18 hours. The solvent is then removed by evaporation under reduced pressure and the residue is taken up in water (30 mL), adjusted to slightly acid pH by adding 6N HCl and then extracted with chloroform (3×30 mL). The organic phases are collected and dried over anhydrous MgSO4. After filtration, the filtrate is evaporated to dryness and the expected compound is obtained in the form of an oil used directly in the next Step.

출처