Aspirin → 4-(3-Thioxo-3H-1,2-dithiol-5-yl)phenyl 2-acetoxybenzoate

HRID 18628

Reaktionsgleichung

Reaktionsgleichung von HRID 18628
[C:1]([O:4][C:5]1[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].OC1C2N=NNC=2C=CC=1.C1CCC(N=C=NC2CCCCC2)CC1.O[C:40]1[CH:45]=[CH:44][C:43]([C:46]2[S:50][S:49][C:48](=[S:51])[CH:47]=2)=[CH:42][CH:41]=1>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([O:9][C:40]1[CH:41]=[CH:42][C:43]([C:46]2[S:50][S:49][C:48](=[S:51])[CH:47]=2)=[CH:44][CH:45]=1)=[O:8])(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 2244AspirinHCID 10868DicyclohexylcarbodiimideHCID 3082127Desmethylanethol trithioneHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 117180344-(3-Thioxo-3H-1,2-dithiol-5-yl)phenyl 2-acetoxybenzoateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To the solution of 1 (acetylsalicylic acid, 416 mg, 2.31 mmol) in 40 mL of dimethylformamide, hydroxybenzotriazole (343 mg, 2.54 mmol) and DCC (523 mg, 2.54 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 5-p-hydroxyphenyl-1,2-dithiole-3-thione (2; 574 mg, 2.54 mmol) was added and stirred for 1 h at 0° C. and 3 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, dried on anhydrous MgSO4, filtered and the solvent evaporated. The crude product was loaded on a silica gel open column and eluted with ethyl ether/petroleum ether (1/1), from which 4-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-acetoxybenzoate (3) was obtained (354 mg, 40% yield).

Aufarbeitung

  1. stirringstirred for 1 h at 0° C. and 3 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
  7. dry with materialdried on anhydrous MgSO4
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. washeluted with ethyl ether/petroleum ether (1/1), from which 4-(5-thioxo-5H-1,2-dithiol-3-yl)phenyl 2-acetoxybenzoate (3)
  11. customwas obtained (354 mg, 40% yield)

Quellen und Nachweise

ORD-Eintrag
ord-0784ea4004a047fb97965e31f554cde6
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741359B2

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