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

HRID 18626

Reaktionsgleichung

Reaktionsgleichung von HRID 18626
[CH:1]1[CH:2]=[CH:3][C:4]([NH:11][C:12]2[C:13]([Cl:19])=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=1.OC1C2N=NNC=2C=CC=1.C1CCC(N=C=NC2CCCCC2)CC1.O[C:46]1[CH:54]=[CH:53][C:49]([C:50]([NH2:52])=[O:51])=[CH:48][CH:47]=1>CN(C)C=O.C(Cl)(Cl)Cl>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[NH:11][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=1[CH2:7][C:8]([O:10][C:46]1[CH:54]=[CH:53][C:49]([C:50](=[O:51])[NH2:52])=[CH:48][CH:47]=1)=[O:9]

Komponenten

7

Edukt 4

HCID 3033DiclofenacHCID 10868DicyclohexylcarbodiimideHCID 650524-HydroxybenzamideHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 593455914-Carbamoylphenyl 2-[2-(2,6-dichlorophenylamino)-phenyl]acetateAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-efdd765be6a748e18147c7442f20519c
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741359B2

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