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

HRID 1801904Notes

Reaction equation

HRID 1801904 reaction equation
[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

Participants

5

Reactant 2

HCID 7268Diethyl OxalateHCID 666116532-Amino-4-iodobenzamide

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-9079f46b33d74e89952bc800ead3f45b
Source dataset
uspto-grants-2013_01
Patent number
US08349851B2

Reaction notes

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