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

HRID 1199644Notes

Reaction equation

HRID 1199644 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 4M 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-bd54388f52fc411780ce1beb86908fe8
Source dataset
uspto-grants-1990_02
Patent number
US04902686

Reaction notes

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