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

HRID 569805Notes

Reaction equation

HRID 569805 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[NH:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:3])[NH2:2].[O:18]1CCOC[CH2:19]1>>[Cl:10][C:7]1[CH:6]=[C:5]2[C:4]([C:1](=[O:3])[NH:2][C:19](=[O:18])[N:11]2[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 11780149Ethyl N-(2-carbamoyl-5-chlorophenyl)aminoacetate

Product 1

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

Conditions

Temperature
150 °C

Procedure

Ethyl N-(2-carbamoyl-5-chlorophenyl)aminoacetate (357 g) and N,N'-carbonyldiimidazole (451 g) were dissolved in 1,4-dioxane (1.5 l) and 1,4-dioxane was concentrated to a bout 0.5 l by distillation. The resulting mixture was stirred at 150° C. for 30 minutes. After cooling, the precipitated crystals were collected by filtration and washed with ethanol to give ethyl 2-(7-chloro-1,2,3,4-tetrahydro-2,4-dioxoquinazolin-1-yl)acetate (353 g).

Workup

  1. concentration1,4-dioxane was concentrated to a bout 0.5 l by distillation
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-8bfdfc93843e401b8d0b99e4ec7b37c3
Source dataset
uspto-grants-1988_03
Patent number
US04734419

Reaction notes

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