Propionic Acid → HCID 59427835, Verbindung

HRID 502542

Reaktionsgleichung

Reaktionsgleichung von HRID 502542
C(O)(=[O:4])CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:25]([CH2:28]C)[CH2:26][CH3:27])C.[NH2:30][C:31]1[S:32][C:33]([C:42]([O:44][CH2:45][CH3:46])=[O:43])=[C:34]([CH3:41])[C:35]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37]>C1(C)C=CC=CC=1.[Cl-].[Na+].O>[CH2:45]([O:44][C:42]([C:33]1[S:32][C:31]([NH:30][C:28]([NH:25][CH2:26][CH3:27])=[O:4])=[C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:34]=1[CH3:41])=[O:43])[CH3:46]

Komponenten

7

Edukt 4

HCID 1032Propionic AcidHCID 8471TriethylamineHCID 78537Diethyl 5-amino-3-methylthiophene-2,4-dicarboxylateHCID 199401P,P-Diphenylphosphinic azide

Produkt 1

HCID 59427835HCID 59427835, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A mixture of propionic acid (0.8 ml, 10 mol), diphenylphosphoryl azide (2.22 ml, 10.3 mmol) and triethylamine (1.39 ml, 10 mmol) in toluene (15 ml) was refluxed for 90 minutes. The mixture was then cooled to below 40° C., and a solution of ethyl 2-amino-5-(ethoxycarbonyl)-4-methylthiophene-3-carboxylate (1.76 g, 6.85 mmol) in toluene (10 ml) was added, the mixture refluxed for 24 hours. The reaction mixture was diluted with brine, and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. Solvent was removed under reduced pressure, and the residue purified by column chromatography, eluting with ethyl acetate/hexane 1:6 to 1:4, to provide ethyl 5-(ethoxycarbonyl)-2-[(ethylamino)carbonylamino]-4-methylthiophene-3-carboxylate. The structure was confirmed by 1H NMR and mass spectrometry.

Aufarbeitung

  1. temperaturewas refluxed for 90 minutes
  2. temperatureThe mixture was then cooled to below 40° C.
  3. temperaturethe mixture refluxed for 24 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customSolvent was removed under reduced pressure
  8. customthe residue purified by column chromatography
  9. washeluting with ethyl acetate/hexane 1:6 to 1:4

Quellen und Nachweise

ORD-Eintrag
ord-5d18453330c54bf69d0ca83ae9abd1ee
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776868B2

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