Reacción #46911

Ecuación de reacción

4-hydroxybenzamide

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

ibuprofen

hydroxybenzotriazole

DCC

→

4-thiocarbamoylphenyl 2-(4-isobutylphenyl)propanoate

Rendimiento 40.0%

Disolventes

ethyl acetate

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred for 1 h at 0° C. and 2 h at room temperature
2. 2
   FiltraciónAfter filtration
3. 3
   Otrothe filtrate was evaporated under reduced pressure
4. 4
   Otroto remove the solvent
5. 5
   OtroThe oily residue thus obtained
6. 6
   Lavadothe organic layer was washed with brine, with NaHCO3 5%, with citric acid 10%
7. 7
   Secadothan dried on anhydrous MgSO4
8. 8
   Filtraciónfiltered
9. 9
   Otrothe solvent evaporated
10. 10
    Lavadoeluted with CH2Cl2/MeOH (9.5/0.5), from which 4-carbamoylphenyl 2-(4-isobutylphenyl)propanoate (3)
11. 11
    Otrowas obtained (2.48 g, 40% yield)

Procedimiento

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).

Fuente