Potassium Carbonate → HCID 22252247, Verbindung

HRID 1611963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1611963
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[O:11][C:7]=2[C:6]([NH2:13])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:21][CH2:22][O:23][CH2:24][CH2:25]I>CN(C=O)C>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[O:11][C:7]=2[C:6]([N:13]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 34307791-Iodo-2-(2-iodoethoxy)ethaneHCID 22252238HCID 22252238, Verbindung

Produkt 1

HCID 22252247HCID 22252247, VerbindungAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of 800 mg (4.47 mmol) 4-methoxy-benzooxazole-2,7-diamine in 40 ml DMF at room temperature were added 2.47 g (17.9 mmol) potassium carbonate and 2.18 g (6.70 mmol) 1-iodo-2-(2-iodo-ethoxy)-ethane and the mixture heated at 60° C. for 48 h. After cooling to room temperature the mixture was poured onto water and extracted three times with ethyl acetate. The combined organic phases were washed with brine, then dried over sodium sulphate and concentrated in vacuo. Flash chromatography (2/98 methanol/dichloromethane, then 10/90 methanol/dichloromethane) afforded 585 mg (53%) 4-methoxy-7-morpholin-4-yl-benzooxazol-2-ylamine as a light brown solid. ES-MS m/e (%): 250 (M+H+, 100).

Aufarbeitung

  1. temperatureAfter cooling to room temperature the mixture
  2. additionwas poured onto water
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-afdc7b2623844dd6b0d59e2767512259
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06992083B2

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