Phosgene → 3-Benzyloxy-5,6,7,8-tetrafluoro-1H-quinazoline-2,4-dione

HRID 2270244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2270244
[NH2:1][C:2]1[C:18]([F:19])=[C:17]([F:20])[C:16]([F:21])=[C:15]([F:22])[C:3]=1[C:4]([NH:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5].[C:23](Cl)(Cl)=[O:24]>O1CCOCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:8]([O:7][N:6]1[C:4](=[O:5])[C:3]2[C:2](=[C:18]([F:19])[C:17]([F:20])=[C:16]([F:21])[C:15]=2[F:22])[NH:1][C:23]1=[O:24])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

6

Edukt 2

HCID 6371PhosgeneHCID 226328792-Amino-N-benzyloxy-3,4,5,6-tetrafluoro-benzamide

Produkt 1

HCID 226328803-Benzyloxy-5,6,7,8-tetrafluoro-1H-quinazoline-2,4-dioneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 2-amino-N-benzyloxy-3,4,5,6-tetrafluoro-benzamide (Example V-3, 1.72 g, 5.47 mmol) in 1,4-dioxane (50 mL) was reacted with a 20% solution of phosgene (4.25 mL, 8.00 mmol) in toluene and heated to 80° C. in a sealed tube for 18 hours. The mixture was then cooled, diluted with ethyl acetate, and washed with saturated aqueous NaHCO3. The organic layer was dried with magnesium sulfate and concentrated. The residue was triturated with diethyl ether and filtered to provide 0.95 g of the title compound as a solid.

Aufarbeitung

  1. temperatureThe mixture was then cooled
  2. washwashed with saturated aqueous NaHCO3
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was triturated with diethyl ether
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-05129559f87342548745dad6af4887b2
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06331538B1

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