Diethyl (ethoxymethylene)malonate → Diethyl[(4-quinazolinylamino)methylene]propanedioate

HRID 2296437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2296437
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.C(O[CH:15]=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])C>CN(C)C=O>[CH2:20]([O:19][C:17](=[O:18])[C:16](=[CH:15][NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1)[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:21]

Komponenten

4

Edukt 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 847594-Aminoquinazoline

Produkt 1

HCID 13060467Diethyl[(4-quinazolinylamino)methylene]propanedioateAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 4-aminoquinazoline (11.6 g) and diethyl ethoxymethylenepropanedioate (19.0 g) in N,N-dimethylformamide (40 ml) was stirred for 1 hour and 20 minutes at 160° C. and then cooled to 0° C. to precipitate crystals. To the mixture was added small volume of water with stirring. The crystals were separated by filtration, washed with water, dried overnight under reduced pressure and dissolved in ethyl acetate. The resultant solution was dried over anhydrous magnesium sulfate and recrystallized from a mixture of ethyl acetate and hexane to give crystalline diethyl[(4-quinazolinylamino)methylene]propanedioate (22.7 g).

Aufarbeitung

  1. temperaturecooled to 0° C.
  2. customto precipitate crystals
  3. additionTo the mixture was added small volume of water
  4. stirringwith stirring
  5. customThe crystals were separated by filtration
  6. washwashed with water
  7. customdried overnight under reduced pressure
  8. dissolutiondissolved in ethyl acetate
  9. dry with materialThe resultant solution was dried over anhydrous magnesium sulfate
  10. customrecrystallized from a mixture of ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-d810b5dcabbb430ea6386aa090eaaecd
Quelldatensatz
uspto-grants-1984_01
Patentnummer
US04429126

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