Réaction #46904

Équation de réaction

4-hydroxybenzamide

diclofenac

hydroxybenzotriazole

DCC

→

4-carbamoylphenyl 2-[2-(2,6-dichlorophenylamino)-phenyl]acetate

Rendement 17.0%

Solvants

chloroform

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred for 1 h at 0° C.
2. 2
   Autreat room temperature
3. 3
   FiltrationAfter filtration
4. 4
   Autrethe filtrate was evaporated under reduced pressure
5. 5
   Autrethe oily residue thus obtained
6. 6
   Lavagethe organic layer was washed with brine
7. 7
   Séchagedried on anhydrous MgSO4
8. 8
   Filtrationfiltered
9. 9
   Autrethe solvent evaporated
10. 10
    Lavageeluted with CH2Cl2/MeOH (9/1), from which 4-carbamoylphenyl 2-(2-(2,6-dichlorophenylamino)phenyl)acetate (5)
11. 11
    Autrewas obtained (212 mg, 17% yield)

Mode opératoire

To the solution of 1 (diclofenac, 890 mg, 3.0 mmol) in 50 mL of N,N-dimethylformamide, hydroxybenzotriazole (445 mg, 3.3 mmol) and DCC (680 mg, 3.3 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 4-hydroxybenzamide (4, 616 mg, 4.5 mmol) was added and stirred for 1 h at 0° C. and 3 hs at room temperature. After filtration, the filtrate was evaporated under reduced pressure and the oily residue thus obtained was dissolved in chloroform; the organic layer was washed with brine, dried on anhydrous MgSO4, filtered and the solvent evaporated. The crude product 5 was loaded on a silica gel open column and eluted with CH2Cl2/MeOH (9/1), from which 4-carbamoylphenyl 2-(2-(2,6-dichlorophenylamino)phenyl)acetate (5) was obtained (212 mg, 17% yield).

Source