Diclofenac → 4-Isothiocyanatophenyl 2-(2-(2,6-dichlorophenylamino)phenyl)acetate

HRID 44170

Reaktionsgleichung

Reaktionsgleichung von HRID 44170
[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.O[C:21]1[C:29]2N=N[NH:26][C:25]=2[CH:24]=[CH:23][CH:22]=1.C1CCC(N=C=NC2CCCCC2)CC1.OC1C=CC(C2S[S:55][C:54](=S)C=2)=CC=1>CN(C)C=O.C(OCC)(=O)C>[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:22]1[CH:23]=[CH:24][C:25]([N:26]=[C:54]=[S:55])=[CH:29][CH:21]=1)=[O:9]

Komponenten

7

Edukt 4

HCID 3033DiclofenacHCID 10868DicyclohexylcarbodiimideHCID 3082127Desmethylanethol trithioneHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 250657704-Isothiocyanatophenyl 2-(2-(2,6-dichlorophenylamino)phenyl)acetateAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To the solution of 1 (diclofenac, 1717 mg, 5.8 mmol) in 60 mL of dimethylformamide, hydroxybenzotriazole (862 mg, 6.38 mmol) and DCC (1316 mg, 6.38 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 4-hydroxyphenylisothiocyanate (2; 965 mg, 6.38 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 and the precipitate was removed. The solvent was evaporated and the crude product was loaded on a silica gel open column and eluted with chloroform/n-hexane 9:1, from which 4-isothiocyanatophenyl 2-(2-(2,6-dichlorophenylamino)phenyl)acetate (3) was obtained (580 mg, 23% yield).

Aufarbeitung

  1. stirringstirred for 1 h at 0° C. and 2 h at room temperature
  2. filtrationAfter filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customto remove the solvent
  5. customThe oily residue thus obtained
  6. customthe precipitate was removed
  7. customThe solvent was evaporated
  8. washeluted with chloroform/n-hexane 9:1, from which 4-isothiocyanatophenyl 2-(2-(2,6-dichlorophenylamino)phenyl)acetate (3)
  9. customwas obtained (580 mg, 23% yield)

Quellen und Nachweise

ORD-Eintrag
ord-206a10ec26d64b0c904bc790354ed986
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541398B2

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