Ethanol → Ethyl (7-chloro-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)acetate

HRID 1532431Notes

Reaction equation

HRID 1532431 reaction equation
[C:1]([CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:15])[CH:13]=2)[C:8](=[O:16])[NH:7][C:6]1=[O:17])([OH:3])=[O:2].S(Cl)(Cl)=O.[CH2:22](O)[CH3:23]>S(=O)(=O)(O)O>[Cl:15][C:12]1[CH:13]=[C:14]2[C:9]([C:8](=[O:16])[NH:7][C:6](=[O:17])[N:5]2[CH2:4][C:1]([O:3][CH2:22][CH3:23])=[O:2])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 10978024HCID 10978024, compound

Product 1

HCID 9838691Ethyl (7-chloro-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)acetateYield 75.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a suspension of 1-carboxymethyl-7-chloro-2,4(1H, 3H)-quinazolinedione (I) (0.5 g) in ethanol (10 ml) was added thionyl chloride (0.35 g) at 0° C. After one drop of concentrated sulfuric acid was added to the solution, the solution was refluxed for 7 hours, and cooled. The resulting crystal was collected by filtration, washed with ethanol and dried under vacuum to give 0.42 g of the desired compound (yield, 75.8%).

Workup

  1. temperaturethe solution was refluxed for 7 hours
  2. temperaturecooled
  3. filtrationThe resulting crystal was collected by filtration
  4. washwashed with ethanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ed527cda59354c51b0d24a5f6b205802
Source dataset
uspto-grants-2001_03
Patent number
US06201121B1

Reaction notes

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