Diclofenac → 4-Carbamoylphenyl 2-[2-(2,6-dichlorophenylamino)-phenyl]acetate

Temperature

0 °C

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).

1. stirringstirred for 1 h at 0° C.
2. customat room temperature
3. filtrationAfter filtration
4. customthe filtrate was evaporated under reduced pressure
5. customthe oily residue thus obtained
6. washthe organic layer was washed with brine
7. dry with materialdried on anhydrous MgSO4
8. filtrationfiltered
9. customthe solvent evaporated
10. washeluted with CH2Cl2/MeOH (9/1), from which 4-carbamoylphenyl 2-(2-(2,6-dichlorophenylamino)phenyl)acetate (5)
11. customwas obtained (212 mg, 17% yield)

ORD record

ord-e02319aa71c74df7a7d37a8e358774bf

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541398B2