Diethyl Oxalate → Ethyl 7-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate

HRID 1424416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1424416
[NH2:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[C:12](OCC)(=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)(=O)C.O>[I:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:6][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:1]2)=[CH:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 7268Diethyl OxalateHCID 666116532-Amino-4-iodobenzamide

Produkt 1

HCID 136386213Ethyl 7-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 2-amino-4-iodobenzamide (1.0 g, 3.61 mmol) in glacial acetic acid (10 mL) at rt was added diethyl oxalate (5 mL). The mixture was heated at 120° C. for 24 h. The mixture was cooled to rt and diluted with H2O until a precipitate formed. The precipitate was removed by filtration, washed with H2O, and dried under high vacuum for several hours to afford ethyl 7-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate (1.0 g, 76%) as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 1.36 (t, 3H), 4.48 (q, 2H), 7.90 (d, 1H), 7.95 (d, 1H), 8.20 (d, 1H), 8.28 (s, 1H), 12.78 (s, 1H); LC-MS (ESI) m/z 330 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was cooled to rt
  2. customformed
  3. customThe precipitate was removed by filtration
  4. washwashed with H2O
  5. customdried under high vacuum for several hours

Quellen und Nachweise

ORD-Eintrag
ord-89ef7729089b4429938eeae0bc99c5b8
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927711B2

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