Dimethylformamide → 7-(Benzyloxy)-4-chloroquinazoline

HRID 454085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454085
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[NH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.S(Cl)([Cl:27])=O>>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:27])=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1357631107-(Benzyloxy)-3,4-dihydroquinazolin-4-one

Produkt 1

HCID 220309237-(Benzyloxy)-4-chloroquinazolineAusbeute 89 %

Versuchsvorschrift

A mixture of 7-benzyloxy-3,4-dihydroquinazolin-4-one (11 g, 43.6 mmol) and DMF (1 ml) in thionyl chloride (100 ml) was heated at reflux for 1.5 hours. Excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene. The residue was partitioned between methylene chloride and water and saturated aqueous sodium hydrogen carbonate was added until the aqueous layer was at about pH9. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated to give 7-benzyloxy-4-chloroquinazoline (10.5 g, 89%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. customExcess thionyl chloride was removed by evaporation
  4. customthe residue azeotroped with toluene
  5. customThe residue was partitioned between methylene chloride and water and saturated aqueous sodium hydrogen carbonate
  6. additionwas added until the aqueous layer
  7. customThe organic layer was separated
  8. washwashed with water, brine
  9. dry with materialdried (MgSO4)
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d13674a1f50940ca8b287a6be7ce52c7
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492560B2

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