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1,1'-Carbonyldiimidazole → 4,5-Dihydro-7H-imidazo[4,5,1-jk][4,1]benzoxazepine-2,7(1H)-dione

HRID 1698540
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1698540
[NH2:1][C:2]1[C:12]2[NH:11][CH2:10][CH2:9][O:8][C:7](=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:14](N1C=CN=C1)(N1C=CN=C1)=[O:15]>C1COCC1>[NH:1]1[C:2]2=[CH:3][CH:4]=[CH:5][C:6]3=[C:12]2[N:11]([CH2:10][CH2:9][O:8][C:7]3=[O:13])[C:14]1=[O:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 672729029-Amino-2,3-dihydro-4,1-benzoxazepin-5(1H)-one

Produkt 1

HCID 672729594,5-Dihydro-7H-imidazo[4,5,1-jk][4,1]benzoxazepine-2,7(1H)-dioneAusbeute 123,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 200 mg (1.13 mmol) of 9-amino-2,3-dihydro-4,1-benzoxazepin-5(1H)-one in 20 mL of THF was added 280 mg (2 mmol) of 1,1′-carbonyldiimidazole and the reaction mixture was stirred overnight at room temperature. The reaction mixture was heated at 50° C. for 4 h and allowed to cool to room temperature. The reaction was concentrated in vacuo and the residue was dissolved in a mixture of ethyl acetate/n-hexane (1:1) and washed with water. The organics were dried over sodium sulfate, filtered, and concentrated in vacuo to give 286 mg (1.40 mmol, 70%) of the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture was heated at 50° C. for 4 h
  2. temperatureto cool to room temperature
  3. concentrationThe reaction was concentrated in vacuo
  4. dissolutionthe residue was dissolved in a mixture of ethyl acetate/n-hexane (1:1)
  5. washwashed with water
  6. dry with materialThe organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e4f9eca2ff744d91aed79647108833ce
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08163935B2

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