Hydrochloric Acid → Methyl 2-amino-4-oxo-4,4a-dihydroquinazoline-7-carboxylate

HRID 449336

Reaktionsgleichung

Reaktionsgleichung von HRID 449336
Cl.[NH2:2][C:3]1[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][C:4]=1[C:5](OC)=[O:6].[N:17]#[C:18][NH2:19]>C(#N)C>[NH2:19][C:18]1[N:2]=[C:3]2[CH:4]([C:5](=[O:6])[N:17]=1)[CH:9]=[CH:10][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:12]2

Komponenten

5

Edukt 3

HCID 313Hydrochloric Acid2×HCID 9864CyanamideHCID 79336Dimethyl aminoterephthalate

Produkt 1

HCID 59496681Methyl 2-amino-4-oxo-4,4a-dihydroquinazoline-7-carboxylateAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Concentrated hydrogen chloride aqueous solution (800 μl, 26.1 mmol) was added to a solution of dimethyl 2-aminoterephthalate (1.82 g, 8.69 mmol), and cyanamide (658 mg, 15.6 mmol) in acetonitrile (20 mL). After the HCl addition, the reaction mixture became slurry and it was heated at 80° C. overnight. The reaction mixture was allowed to cool to room temperature and became thick slurry; then the solids were filtered, washed with ethyl ether, and dried to give the crude product (1.50 g, 78.7%) as a white solid. 1H NMR (300 MHz, DMSO): δ 3.9 (s, 3H), 7.84 (dd, 1H), 7.99 (d, 1H), 8.09 (d, 1H), 8.55 (b, 2H); Analytic LCMS (M+H)+: m/z=220.1.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. filtrationthen the solids were filtered
  3. washwashed with ethyl ether
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2a35507492f3406292ba8071725f8f8f
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481732B2

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