Ethyl Acetate → 2-(4,6-Dimethoxypyrimidine-2-ylcarbonyl)aniline

HRID 1163453

Reaktionsgleichung

Reaktionsgleichung von HRID 1163453
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13]C=2C)[N:4]=1.C(OCC)(=[O:23])C.O=[O+][O-]>O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]([C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH2:13])=[O:23])[N:4]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 24823OzoneHCID 129793683-(4,6-Dimethoxypyrimidine-2-yl)-2-methylindole2×

Produkt 1

HCID 178567502-(4,6-Dimethoxypyrimidine-2-ylcarbonyl)anilineAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

In a reactor were placed 0.60 g (22 m moles) of 3-(4,6-dimethoxypyrimidine-2-yl)-2-methylindole and 20 ml of ethyl acetate. Thereinto was blown ozone at 0° C. to 10° C. for 4 hours. Thin-layer chromatography was conducted to confirm the disappearance of 3-(4,6-dimethoxypyrimidine-2-yl)-2-methylindole and complete a reaction. Then, the reaction mixture was heated to room temperature and concentrated. To the concentrate were added 20 ml of methanol and 5 ml of 6 N hydrochloric acid, and refluxing was made for 1 hour with heating. After the completion of the reaction, the reaction mixture was cooled to room temperature. 100 ml of water was added. The mixture was made alkaline with an aqueous sodium hydroxide solution, and extraction was made with ethyl acetate. The organic layer was concentrated. The concentrate was subjected to column chromatography separation to obtain 0.26 g (10 m moles) of 2-(4,6-dimethoxypyrimidine-2-ylcarbonyl)aniline. Yield: 46%

Aufarbeitung

  1. customIn a reactor were placed
  2. customat 0° C. to 10° C.
  3. customfor 4 hours
  4. customa reaction
  5. concentrationconcentrated
  6. additionTo the concentrate were added 20 ml of methanol and 5 ml of 6 N hydrochloric acid
  7. temperaturerefluxing
  8. temperaturewith heating
  9. customAfter the completion of the reaction
  10. temperaturethe reaction mixture was cooled to room temperature
  11. extractionwith an aqueous sodium hydroxide solution, and extraction
  12. concentrationThe organic layer was concentrated
  13. customThe concentrate was subjected to column chromatography separation

Quellen und Nachweise

ORD-Eintrag
ord-fa89b47c1817472d9326efc09dbbaaf3
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820861B2

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