Isatoic Anhydride → 3-Ethyl-2,4(1H,3H)-quinazolinedione

HRID 868678Notes

Reaction equation

HRID 868678 reaction equation
Cl.[CH2:2]([NH2:4])[CH3:3].[OH-].[Na+].[C:7]12[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=1)[NH:12][C:11](=O)[O:10][C:8]2=[O:9]>C(Cl)Cl>[CH2:2]([N:4]1[C:8](=[O:9])[C:7]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]1=[O:10])[CH3:3]

Participants

5

Reactant 3

HCID 8359Isatoic AnhydrideHCID 11198Ethylamine hydrochlorideHCID 14798Sodium Hydroxide2×

Product 1

HCID 7474393-Ethyl-2,4(1H,3H)-quinazolinedioneYield 27.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 12.23 g of ethylamine hydrochloride, 35 ml 4M sodium hydroxide and 175 ml methylene chloride was added 16.3 g isatoic anhydride. This mixture was stirred for 4 hours and the aqueous phase was made basic with 4 M sodium hydroxide. The organic phase was evaporated in vacuo. The residue was dissolved in 300 ml of tetrahydrofuran (THF) and 75 ml phosgene solution (20% in toluene) was added. The resulting mixture was stirred at 80° C. for two hours. The precipitate was filtered off and the mother liquor was evaporated leaving 5.2 g of the title compound. M.p. 189.8°-189.9° C.

Workup

  1. customThe organic phase was evaporated in vacuo
  2. dissolutionThe residue was dissolved in 300 ml of tetrahydrofuran (THF)
  3. addition75 ml phosgene solution (20% in toluene) was added
  4. stirringThe resulting mixture was stirred at 80° C. for two hours
  5. filtrationThe precipitate was filtered off
  6. customthe mother liquor was evaporated

Sources & evidence

ORD record
ord-ee19b621eeb949a1b8dd0b2289aa2e5b
Source dataset
uspto-grants-1988_10
Patent number
US04780539

Reaction notes

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