Acetic Anhydride → 6-fluoro-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3-(2-methyl-phenyl)-3H-quinazolin-4-one

HRID 380384

Reaktionsgleichung

Reaktionsgleichung von HRID 380384
[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[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])[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>O.[Cl-].[Zn+2].[Cl-]>[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[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])[C:5]2=[O:20]

Komponenten

6

Edukt 3

HCID 7918Acetic AnhydrideHCID 634674(3H)-Quinazolinone, 6-fluoro-2-methyl-3-(2-methylphenyl)-HCID 27631912-Methyl-1,3-thiazole-4-carbaldehyde

Produkt 1

HCID 544906406-fluoro-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3-(2-methyl-phenyl)-3H-quinazolin-4-oneAusbeute 21,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Anhydrous zinc chloride (0.136 g, 1.0 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, then dioxane (10 mL) was added. To this mixture was added 6-fluoro-2-methyl-3-(2-methyl-phenyl)-3H-quinazolin-4-one (0.134 g, 0.5 mmol), acetic anhydride (0.141 mL, 1.5 mmol), and 2-methylthiazole-4-carboxaldehyde (0.191 g, 1.5 mmol). The reaction was refluxed 3.5 h, cooled to ambient temperature, and diluted with water. 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 was triturated with ether, filtered and dried to afford 0.04 g (21%) of 6-fluoro-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3-(2-methyl-phenyl)-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
  3. additiondioxane (10 mL) was added
  4. temperatureThe reaction was refluxed 3.5 h
  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. customThis residue was triturated with ether
  11. filtrationfiltered
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-577ec6d2122b4514b428cabb363d704e
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303615B1

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