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Tetrahydrofuran → 3a,5-dihydro-3H-[1,3]oxazolo[3,4-a]quinoxaline-1,4-dione

HRID 1899955
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1899955
[CH3:1][O:2][C:3](=O)[CH:4]([CH2:15][OH:16])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O.C(N1C=CN=C1)(N1C=CN=C1)=[O:19].C1COCC1>C(N(CC)CC)C>[C:1]1(=[O:19])[N:5]2[C:6]3[C:7]([NH:12][C:15](=[O:16])[CH:4]2[CH2:3][O:2]1)=[CH:8][CH:9]=[CH:10][CH:11]=3
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Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 682631,1'-Carbonyldiimidazole2×HCID 10014501HCID 10014501, Verbindung

Produkt 1

HCID 104428883a,5-dihydro-3H-[1,3]oxazolo[3,4-a]quinoxaline-1,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To 3-hydroxymethyl-1,2,3,4-tetrahydroquinoxalin-2-one (IV, EXAMPLE 286, 1.35 g), 1.00 g of carbonyldiimidazole, and 30 ml of THF are added 1.64 ml of triethylamine. The reaction is stirred at 20°-25° for 6 hr, then at 80° for 18 hr, at which time an additional 0.11 g carbonyldiimidazole are added. Heating is continued for another 6 hr, at which time the reaction mixture is cooled and the solvent is removed under reduced pressure. The residue is partitioned between methylene chloride and water, the organic layers are dried over sodium sulfate and concentrated. The residue is crystallized from methanol/dichloromethane to give the title compound, mp 230°-231°; MS (m/z) at 204; NMR (CDCl3) 4.60, 4.78, 6.93, 7.19, 7.82 and 8.48 δ.

Aufarbeitung

  1. waitat 80° for 18 hr
  2. temperatureHeating
  3. waitis continued for another 6 hr, at which time
  4. temperaturethe reaction mixture is cooled
  5. customthe solvent is removed under reduced pressure
  6. customThe residue is partitioned between methylene chloride and water
  7. dry with materialthe organic layers are dried over sodium sulfate
  8. concentrationconcentrated
  9. customThe residue is crystallized from methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-8c0c705e0225498792a77c2a834aeeea
Quelldatensatz
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05574038

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