Hydrochloric Acid → Ethyl 6-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate

HRID 606477Notes

Reaction equation

HRID 606477 reaction equation
[NH2:1][C:2]([C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:3].CC[O-].[Na+].Cl>C(O)C>[I:10][C:8]1[CH:9]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:1][C:2]2=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 66769092Ethyl ((2-(aminocarbonyl)-4-iodophenyl)amino)(oxo)acetate

Product 1

HCID 136014453Ethyl 6-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of ethyl ((2-(aminocarbonyl)-4-iodophenyl)amino)(oxo)acetate (20.9 g, 57.7 mmol) in ethanol (300 mL) was added dropwise sodium ethylate (20% ethanol solution, 21.6 g, 63.5 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into 0.3N hydrochloric acid (600 mL) under ice-cooling, and the precipitated insoluble material was collected by filtration. The filtered cake was washed with water and ethanol to give ethyl 6-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate as a pale-pink powder (17.0 g, 86%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationthe precipitated insoluble material was collected by filtration
  4. washThe filtered cake was washed with water and ethanol

Sources & evidence

ORD record
ord-aa3b8334577c4e91b405953f3d1078b4
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

Loading…