Phosphorus oxychloride → Ethyl 4-chloroquinazoline-2-carboxylate

HRID 1245062Notes

Reaction equation

HRID 1245062 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:15][C:14](=O)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:19])=O>>[CH2:1]([O:3][C:4]([C:6]1[N:15]=[C:14]([Cl:19])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135437466Ethyl 4-oxo-3,4-dihydroquinazoline-2-carboxylate

Product 1

HCID 3477840Ethyl 4-chloroquinazoline-2-carboxylateYield 90%

Procedure

2.18 g (10 mmol) of 2-ethoxycarbonylquinazolin-4-one was suspended in 20 ml of phosphorus oxychloride. The mixture was refluxed for one hour, and the solvent was removed by rotary evaporation. The resulting residue was dissolved in ethyl acetate, and the obtained solution was washed with saturated sodium bicarbonate solution three times, dried over anhydrous sodium sulfate, filtered, and evaporated to give 2.13 g (90% mmol) of 2-ethoxycarbonyl-4-chloroquinazoline as a pale-yellow solid. LC/MS (m/z) 237 (M+1)+.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. customthe solvent was removed by rotary evaporation
  3. dissolutionThe resulting residue was dissolved in ethyl acetate
  4. washthe obtained solution was washed with saturated sodium bicarbonate solution three times
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9a36896c6563476ab1001a03acfe1bf2
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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