반응 #46911

반응 방정식

4-hydroxybenzamide

5-p-hydroxyphenyl-1,2-dithiole-3-thione

ibuprofen

hydroxybenzotriazole

DCC

→

4-thiocarbamoylphenyl 2-(4-isobutylphenyl)propanoate

수율 40.0%

용매

ethyl acetate

dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for 1 h at 0° C. and 2 h at room temperature
2. 2
   여과After filtration
3. 3
   기타the filtrate was evaporated under reduced pressure
4. 4
   기타to remove the solvent
5. 5
   기타The oily residue thus obtained
6. 6
   세척the organic layer was washed with brine, with NaHCO3 5%, with citric acid 10%
7. 7
   건조than dried on anhydrous MgSO4
8. 8
   여과filtered
9. 9
   기타the solvent evaporated
10. 10
    세척eluted with CH2Cl2/MeOH (9.5/0.5), from which 4-carbamoylphenyl 2-(4-isobutylphenyl)propanoate (3)
11. 11
    기타was obtained (2.48 g, 40% yield)

실험 절차

To the solution of 1 (ibuprofen, 3.87 g, 18.8 mmol) in 80 mL of dimethylformamide, hydroxybenzotriazole (2.8 g, 20.7 mmol) and DCC (4.27 g, 20.7 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 4-hydroxybenzamide (2, 3.9 g, 28 mmol) was added and stirred for 1 h at 0° C. and 2 h at room temperature. After filtration, the filtrate was evaporated under reduced pressure to remove the solvent. The oily residue thus obtained was dissolved in ethyl acetate; the organic layer was washed with brine, with NaHCO3 5%, with citric acid 10% and than dried on anhydrous MgSO4, filtered and the solvent evaporated. The crude product 3 was loaded on a silica gel open column and eluted with CH2Cl2/MeOH (9.5/0.5), from which 4-carbamoylphenyl 2-(4-isobutylphenyl)propanoate (3) was obtained (2.48 g, 40% yield).

출처