Dimethylformamide → 4-Chloro-2-[(3-phenyl)phenyl]-7-methoxyquinazolin-6-yl acetate

HRID 1808478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1808478
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[C:10]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:18]=1)[NH:9][C:8]2=O)(=[O:3])[CH3:2].CN(C=O)C.O=S(Cl)[Cl:37]>>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[C:10]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:18]=1)[N:9]=[C:8]2[Cl:37])(=[O:3])[CH3:2]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1362032482-[(3-Phenyl)phenyl]-7-methoxy-4-oxo-3,4-dihydroquinazolin-6-yl acetate

Produkt 1

HCID 593618554-Chloro-2-[(3-phenyl)phenyl]-7-methoxyquinazolin-6-yl acetate

Versuchsvorschrift

To a mixture of 2-[(3-phenyl)phenyl]-7-methoxy-4-oxo-3,4-dihydroquinazolin-6-yl acetate (3.6 g, 9.32 mmole) in SOCl2 (40 mL) was added DMF (1 mL) and the reaction was stirred at reflux for 16 h. The mixture was cooled to RT and then the volatiles were removed in vacuo. The crude product was dissolved in CHCl3 (300 mL) and washed with saturated NaHCO3 solution (3×150 mL), water (2×150 mL) and brine (1×150 mL) and dried with Na2SO4. The solution was concentrated in vacuo to yield 4-chloro-2-[(3-phenyl)phenyl]-7-methoxyquinazolin-6-yl acetate (4.0 g, 9.88 mmole). HPLC retention time 11.12 mins. (5-95-13 method).

Aufarbeitung

  1. temperatureat reflux for 16 h
  2. customthe volatiles were removed in vacuo
  3. dissolutionThe crude product was dissolved in CHCl3 (300 mL)
  4. washwashed with saturated NaHCO3 solution (3×150 mL), water (2×150 mL) and brine (1×150 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationThe solution was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-29361a0d2ece4fd1ab6c10607efe5640
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357693B2

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