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Ethyl 2-aminobenzoate → 3-(4-Methylphenyl)quinazoline-2,4(1H,3H)-dione

HRID 1735963
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1735963
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([N:7]=[C:8]=[O:9])=[CH:3][CH:2]=1.[C:11](OCC)(=[O:19])[C:12]1[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH2:14].C[O-].[Na+]>C1(C)C(C)=CC=CC=1>[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([N:7]2[C:11](=[O:19])[C:12]3[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:14][C:8]2=[O:9])=[CH:3][CH:2]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6877Ethyl 2-aminobenzoateHCID 693254-Methylphenyl isocyanateHCID 10942334Sodium Methoxide

Produkt 1

HCID 4788253-(4-Methylphenyl)quinazoline-2,4(1H,3H)-dioneAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of p-tolyl isocyanate (133.2 g, 1.00 mol) in xylene (300 ml) is metered at room temperature into a solution of ethyl anthranilate (165.2 g, 1.00 mol) in xylene (600 ml). After addition is complete, the mixture is stirred at 90° C. for 2.5 hours. 18.0 ml of a 30% strength solution of methanolic sodium methoxide (0.10 mol) are metered in and the mixture is stirred at 90° C. for a further 2 hours, ethanol and methanol being distilled off. After cooling, the product is filtered off with suction and washed with 3×75 ml of xylene. The xylene-moist precipitate is treated with dilute hydrochloric acid and the residual xylene is removed by azeotropic distillation. The product is then filtered off with suction, washed with water and dried. 233.0 g of 3-(4-tolyl)-2,4(1H,3H)-quinazolinedione (yield 92.4% of theory) of melting point 267° C. (lit 265° to 266° C.) are obtained.

Aufarbeitung

  1. additionAfter addition
  2. stirringis stirred at 90° C. for a further 2 hours
  3. distillationethanol and methanol being distilled off
  4. temperatureAfter cooling
  5. filtrationthe product is filtered off with suction
  6. washwashed with 3×75 ml of xylene
  7. additionThe xylene-moist precipitate is treated with dilute hydrochloric acid
  8. customthe residual xylene is removed by azeotropic distillation
  9. filtrationThe product is then filtered off with suction
  10. washwashed with water
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ca8b6f8e4904455197b654be1c078483
Quelldatensatz
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05539114

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