Dimethylformamide → 4-Chloro-6-methoxy-7-(2-(imidazol-1-yl)ethoxy)quinazoline

HRID 454259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454259
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13](=O)[NH:14][CH:15]=[N:16]3)=[CH:11][C:10]=2[O:20][CH3:21])[CH:5]=[CH:4][N:3]=[CH:2]1.S(Cl)([Cl:24])=O.CN(C=O)C>C1(C)C=CC=CC=1>[Cl:24][C:13]1[C:12]2[C:17](=[CH:18][C:9]([O:8][CH2:7][CH2:6][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[C:10]([O:20][CH3:21])[CH:11]=2)[N:16]=[CH:15][N:14]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1354908447-(2-(Imidazol-1-yl)ethoxy)-6-methoxy-3,4-dihydroquinazolin-4-one

Produkt 1

HCID 111412614-Chloro-6-methoxy-7-(2-(imidazol-1-yl)ethoxy)quinazolineAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 7-(2-(imidazol-1-yl)ethoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (412 mg, 1.44 mmol), thionyl chloride (5 ml) and DMF (0.2 ml) was heated at reflux for 1 hour. The mixture was diluted with toluene and the volatiles were removed by evaporation. The residue was suspended in methylene chloride, cooled to 0° C. and aqueous sodium hydrogen carbonate solution was added. The resulting precipitate was collected by filtration and dried under vacuum to give 4-chloro-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline (258 mg, 59%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. customthe volatiles were removed by evaporation
  4. additionaqueous sodium hydrogen carbonate solution was added
  5. filtrationThe resulting precipitate was collected by filtration
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d6d4bc5d73394412a3043ff88904c4d1
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492560B2

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