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

HRID 611476Notes

Reaction equation

HRID 611476 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=O.[O-:19][C:20]#[N:21].[K+]>S1(CCCC1)(=O)=O>[Cl:2][C:3]1[CH:4]=[C:5]2[C:6]([C:7](=[O:9])[NH:21][C:20](=[O:19])[N:12]2[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 111187174-chloro-N-(ethoxycarbonylmethyl)anthranilic acidHCID 11378442Potassium cyanate

Product 1

HCID 9838691Ethyl (7-chloro-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)acetateYield 87%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

Hydrogen chloride is passed into 1 g of 4-chloro-N-(ethoxycarbonylmethyl)anthranilic acid and 1.6 g of potassium cyanate in 20 ml of sulfolane at 50° C. until analysis by HPLC indicates complete conversion. The product is precipitated by addition of water, filtered off, washed with water and dried. 0.95 g (87%) of ethyl 1,2,3,4-tetrahydro-7-chloro-2,4-dioxoquinazolin-1-ylacetate is obtained.

Workup

  1. customThe product is precipitated by addition of water
  2. filtrationfiltered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-7313568f09714fc3a3418ba8d0f60510
Source dataset
uspto-grants-1999_12
Patent number
US06001831

Reaction notes

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