Phosphorus oxychloride → [2-Chloro-4-(3-chlorophenyl)-6-quinazolinyl](4-fluorophenyl)-methanone

HRID 1441454Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441454
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18](=[O:26])[C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH:16]=3)[NH:11][C:10](=O)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.P(Cl)(Cl)([Cl:30])=O>>[Cl:30][C:10]1[N:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[O:26])[CH:16]=2)[N:11]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 686907514-(3-chlorophenyl)-6-(4-fluorobenzoyl)-2(1H)-quinazolinone

Produkt 1

HCID 17976100[2-Chloro-4-(3-chlorophenyl)-6-quinazolinyl](4-fluorophenyl)-methanoneAusbeute 40 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Intermediate 5 ( 0.0528 mol) was added in phosphoryl chloride (200 ml) at room temperature. The mixture was stirred at 100° C. for 3 hours and cooled to room temperature. The solvent was evaporated. The residue was taken up in DCM. The solvent was evaporated till dryness. The residue was taken up in DCM, poured out into ice water, neutralised with K2CO3 solid and extracted with DCM. The organic layer was washed with water, separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was crystallized from 2-propanone. The precipitate was filtered off and dried, yielding 8.5 g (40%) of intermediate 6. The mother layer was evaporated. The residue was purified by column chromatography over silica gel (eluent:toluene/EtOAc 95/5; 15-35 μm). The pure fractions were collected and the solvent was evaporated. A part (0.5 g) of the residue (8.9 g, 42%) was crystallized from 2-propanone. The precipitate was filtered off and dried, yielding 0.3 g of [2-chloro-4-(3-chlorophenyl)-6-quinazolinyl](4-fluorophenyl)-methanone (intermediate 6), mp. 138° C.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customThe solvent was evaporated
  3. customThe solvent was evaporated till dryness
  4. additionpoured out into ice water
  5. extractionextracted with DCM
  6. washThe organic layer was washed with water
  7. customseparated
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from 2-propanone
  12. filtrationThe precipitate was filtered off
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c85b83b02b124e489da4d801fb18b4ca
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655654B2

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