Thionyl Chloride → 4-Chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline

HRID 454010Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454010
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.S(Cl)([Cl:25])=O>CN(C=O)C>[Cl:25][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 178486771HCID 178486771, Verbindung

Produkt 1

HCID 111417924-Chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-hydroxy-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (1.7 g, 5 mmol) and thionyl chloride (25 ml) containing DMF (0.2 ml) was heated at reflux for 3 hours. Excess thionyl chloride was removed by evaporation and by azeotroping with toluene (×2). The residue was suspended in ether and 10% aqueous solution of sodium hydrogen carbonate was added to the mixture. The organic layer was separated, dried (MgSO4) and the solvent removed by evaporation to give 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (1.94 g, quantitative).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customExcess thionyl chloride was removed by evaporation
  4. customby azeotroping with toluene (×2)
  5. addition10% aqueous solution of sodium hydrogen carbonate was added to the mixture
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-0c607c722c8d434bb7aaf4b1807b293e
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492560B2

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