Ibuprofen, (+-)- → 4-Thiocarbamoylphenyl 2-(4-isobutylphenyl)propanoate

HRID 44168

Reaktionsgleichung

Reaktionsgleichung von HRID 44168
[OH:1][C:2]([CH:4]([C:6]1[CH:15]=[CH:14][C:9]([CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:8][CH:7]=1)[CH3:5])=[O:3].OC1C2N=N[NH:22]C=2C=CC=1.C1CCC(N=C=NC2CCCCC2)CC1.O[C:42]1[CH:47]=[CH:46][C:45]([C:48]2[S:52]SC(=S)C=2)=[CH:44][CH:43]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:10]([C:9]1[CH:8]=[CH:7][C:6]([CH:4]([CH3:5])[C:2]([O:1][C:42]2[CH:47]=[CH:46][C:45]([C:48](=[S:52])[NH2:22])=[CH:44][CH:43]=2)=[O:3])=[CH:15][CH:14]=1)[CH:11]([CH3:12])[CH3:13]

Komponenten

7

Edukt 4

HCID 3672Ibuprofen, (+-)-HCID 10868DicyclohexylcarbodiimideHCID 3082127Desmethylanethol trithioneHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 250657684-Thiocarbamoylphenyl 2-(4-isobutylphenyl)propanoateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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).

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. washthe organic layer was washed with brine, with NaHCO3 5%, with citric acid 10%
  7. dry with materialthan dried on anhydrous MgSO4
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. washeluted with CH2Cl2/MeOH (9.5/0.5), from which 4-carbamoylphenyl 2-(4-isobutylphenyl)propanoate (3)
  11. customwas obtained (2.48 g, 40% yield)

Quellen und Nachweise

ORD-Eintrag
ord-460c3c3583bc4692b82a9f35af663085
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541398B2

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