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

HRID 1532432Notes

Reaction equation

HRID 1532432 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(=O)(=O)(O)O.[CH2:23](O)[CH3:24]>>[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][CH2:23][CH3:24])=[O:2])=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 10978024HCID 10978024, compound

Product 1

HCID 9838691Ethyl (7-chloro-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)acetateYield 82%

Procedure

To a suspension of 1-carboxymethyl-7-chloro-2,4(1H, 3H)-quinazolinedione (I) (5 g) in ethanol (50 ml) was added concentrated sulfuric acid (0.96 g) at room temperature, and the reaction solution was refluxed for 19 hours. After the reaction solution was concentrated suitablely to half, water (25 ml) was added, 10% potassium bicarbonate solution (25 g) was further added to adjust to pH 8. The resulting crystal was collected by filtration, washed with water and dried under vacuum to give 4.55 g of the desired compound (yield, 82%).

Workup

  1. temperaturethe reaction solution was refluxed for 19 hours
  2. concentrationAfter the reaction solution was concentrated suitablely to half, water (25 ml)
  3. additionwas added
  4. addition10% potassium bicarbonate solution (25 g) was further added
  5. filtrationThe resulting crystal was collected by filtration
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-0027483723eb409f81cefbcd80022294
Source dataset
uspto-grants-2001_03
Patent number
US06201121B1

Reaction notes

Loading…