Thionyl Chloride → 4-Chloro-7-methoxyquinazolin-6-yl acetate

HRID 403662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 403662
[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]=[CH:10][NH:9][C:8]2=O)(=[O:3])[CH3:2].S(Cl)([Cl:20])=O>CN(C=O)C>[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]=[CH:10][N:9]=[C:8]2[Cl:20])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 1356819606-Acetoxy-7-methoxy-3H-quinazolin-4-one

Produkt 1

HCID 220221604-Chloro-7-methoxyquinazolin-6-yl acetateAusbeute 84,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A mixture of 7-methoxy-4-oxo-3,4-dihydroquinazolin-6-yl acetate (8.7 g, 0.037 mol), thionyl chloride (120 ml, 1.65 mol) and DMF (1 ml) was stirred and heated to 55° C. for 6 hours. The mixture was cooled to room temperature and thionyl chloride was evaporated. The solid was dissolved in chloroform and the solution was washed with sodium bicarbonate and brine, the chloroform was evaporated under reduced pressure to give 7.9 g of a gray product. MS (ESI) m/z: 253 (M+1).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customthionyl chloride was evaporated
  3. dissolutionThe solid was dissolved in chloroform
  4. washthe solution was washed with sodium bicarbonate and brine
  5. customthe chloroform was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d8530beba4094308b604546e3b5b5acf
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748453B2

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