Acetic Anhydride → HCID 49826222, Verbindung

HRID 380383

Reaktionsgleichung

Reaktionsgleichung von HRID 380383
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[N:6]([C:13]1[C:14]([CH3:19])=[N:15][CH:16]=[CH:17][CH:18]=1)[C:5]2=[O:20].C(OC(=O)C)(=O)C.[CH3:28][C:29]1[S:30][CH:31]=[C:32]([CH:34]=O)[N:33]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.[Cl-].[Zn+2].[Cl-].CO>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]=[CH:34][C:32]1[N:33]=[C:29]([CH3:28])[S:30][CH:31]=1)[N:6]([C:13]1[C:14]([CH3:19])=[N:15][CH:16]=[CH:17][CH:18]=1)[C:5]2=[O:20]

Komponenten

8

Edukt 4

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 27631912-Methyl-1,3-thiazole-4-carbaldehydeHCID 22347424HCID 22347424, Verbindung

Produkt 1

HCID 49826222HCID 49826222, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Anhydrous zinc chloride (2.7 g, 20 mmol) was fused with a nitrogen purge in a round bottom flask with an open flame. The reaction vessel was allowed to return to ambient temperature, at which time dioxane (150 mL) was then added. To this mixture was added 6-fluoro-2-methyl-3-(2-methyl-pyridin-3-yl)-3H-quinazolin-4-one (2.6 g, 10 mmol), acetic anhydride (2.8 mL, 30 mmol), and 2-methylthiazole-4-carboxaldehyde (3.7 g, 30 mmol). The reaction was refluxed 2 hours, cooled to ambient temperature, and diluted with water. Sodium carbonate was added until the mixture was basic. The mixture was repeatedly extracted with chloroform. The combined chloroform layer was washed with water and brine and finally dried over sodium sulfate and concentrated to leave a dark residue. This residue treated with methanol and concentrated (effectively azeotroping residual chloroform from the residue) and this process was repeated to leave a brown solid. The solid was triturated with ether (twice), filtered and dried to afford 3.1 g (82%) of 6-fluoro-3-(2-methyl-pyridin-3-yl)-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3H-quinazolin-4-one as tan solid.

Aufarbeitung

  1. custompurge in a round bottom flask with an open flame
  2. customto return to ambient temperature, at which time dioxane (150 mL)
  3. additionwas then added
  4. temperatureThe reaction was refluxed 2 hours
  5. extractionThe mixture was repeatedly extracted with chloroform
  6. washThe combined chloroform layer was washed with water and brine
  7. dry with materialfinally dried over sodium sulfate
  8. concentrationconcentrated
  9. customto leave a dark residue
  10. concentrationconcentrated (
  11. customeffectively azeotroping residual chloroform from the residue) and this process
  12. customto leave a brown solid
  13. customThe solid was triturated with ether (twice),
  14. filtrationfiltered
  15. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d9bfc7c0746c4859865b38fa74c9cf1b
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303615B1

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