Dimethylformamide → 4-Chloro-2-(3-nitrophenyl)quinazolin-6-yl acetate

HRID 1808494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1808494
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)[NH:9][C:8]2=O)(=[O:3])[CH3:2].CN(C=O)C.O=S(Cl)[Cl:32]>>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)[N:9]=[C:8]2[Cl:32])(=[O:3])[CH3:2]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 135796464HCID 135796464, Verbindung

Produkt 1

HCID 569494764-Chloro-2-(3-nitrophenyl)quinazolin-6-yl acetate

Versuchsvorschrift

A suspension of 2-(3-nitrophenyl)-4-oxo-3,4-dihydroquinazolin-6-yl acetate (3.30 g, 10.1 mmol) in SOCl2 (65 mL) was added DMF (2 mL). The mixture was refluxed for 2.5 h, upon which the volatiles were removed in vacuo. The residue was taken up in CHCl3 (450 mL) and washed with sat NaHCO3 (200 ml) and water (200 mL). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to give the product 4-chloro-2-(3-nitrophenyl)quinazolin-6-yl acetate (3.53 g, 10.3 mmol). HPLC retention time 9.748 min.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2.5 h, upon which the volatiles
  2. customwere removed in vacuo
  3. washwashed
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-aea0ca67e5464fd580bbbdecd573efe7
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357693B2

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