Dicyclohexylcarbodiimide → 4-(Isothiocyano)-phenyl 2-(2-methoxynaphthalen-6-yl)propanoate

HRID 18635

Reaktionsgleichung

Reaktionsgleichung von HRID 18635
[CH3:1][C@H:2]([C:15]([OH:17])=[O:16])[C:3]1[CH:8]=[CH:7][C:6]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:5]=2[CH:4]=1.O[C:19]1[C:27]2N=N[NH:24][C:23]=2[CH:22]=[CH:21][CH:20]=1.C1CCC(N=C=NC2CCCCC2)CC1.OC1C=CC(C2S[S:53][C:52](=S)C=2)=CC=1>CN(C)C=O.C(OCC)(=O)C>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:5]2[C:6](=[CH:7][CH:8]=[C:3]([CH:2]([CH3:1])[C:15]([O:17][C:20]3[CH:21]=[CH:22][C:23]([N:24]=[C:52]=[S:53])=[CH:27][CH:19]=3)=[O:16])[CH:4]=2)[CH:9]=1

Komponenten

7

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 156391NaproxenHCID 3082127Desmethylanethol trithioneHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 250657694-(Isothiocyano)-phenyl 2-(2-methoxynaphthalen-6-yl)propanoateAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To the solution of 1 (naproxene, 691 mg, 3 mmol) in 20 mL of dimethylformamide, hydroxybenzotriazole (446 mg, 3.3 mmol) and DCC (619 mg, 3.3 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 4-hydroxyphenylisothiocyanate (2; 500 mg, 3.3 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 dichloromethane, from which 4-(isothiocyano)-phenyl 2-(2-methoxynaphthalen-6-yl)propanoate (3) was obtained (230 mg, 21% 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 dichloromethane, from which 4-(isothiocyano)-phenyl 2-(2-methoxynaphthalen-6-yl)propanoate (3)
  9. customwas obtained (230 mg, 21% yield)

Quellen und Nachweise

ORD-Eintrag
ord-ff81df212f994bafbf6c7bfe90e1cc54
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741359B2

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