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

HRID 1801904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1801904
[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-9079f46b33d74e89952bc800ead3f45b
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349851B2

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