1,1'-Carbonyldiimidazole → 8-(3-(Trifluoromethyl)phenyl)-3H,6H-1,4,5a,8a-tetraazaacenaphthylene-3,5(4H)-dione

HRID 2050509

Reaktionsgleichung

Reaktionsgleichung von HRID 2050509
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[N:15]=[CH:16][C:17]([C:18]([NH2:20])=[O:19])=[C:13]3[NH:12][CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>O1CCOCC1>[F:22][C:2]([F:21])([F:1])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[C:13]4[N:12]([C:23](=[O:24])[NH:20][C:18](=[O:19])[C:17]=4[CH:16]=[N:15]3)[CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 27370934,5-Dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

Produkt 1

HCID 150440768-(3-(Trifluoromethyl)phenyl)-3H,6H-1,4,5a,8a-tetraazaacenaphthylene-3,5(4H)-dioneAusbeute 59,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred mixture of 10.0 g of 4,5-dihydro-7-(3-(trifluoromethyl)phenyl)pyrazolo(1,5-a)pyrimidine-3-carboxamide (prepared as described in Example 8) in 200 ml of dioxane at room temperature under nitrogen is added 20.0 g of 1,1'-carbonyldiimidazole. The mixture is then heated at reflux for 5 hours, and then is cooled and filtered. The filtrate is evaporated to dryness in vacuo and an excess of water is added to the residue. The white solid which forms is collected and is recrystallized from acetonitrile-ethanol to give 6.5 g of the desired product as a white solid, mp 260-262° C.

Aufarbeitung

  1. temperatureThe mixture is then heated
  2. temperatureat reflux for 5 hours
  3. temperatureis cooled
  4. filtrationfiltered
  5. customThe filtrate is evaporated to dryness in vacuo
  6. additionan excess of water is added to the residue
  7. customThe white solid which forms is collected
  8. customis recrystallized from acetonitrile-ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2ae0d4fd3c004d7aa21dbdaea362f2cd
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05013737

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