Ammonia → Quinazolinedione

HRID 1702977Notes

Reaction equation

HRID 1702977 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=O)[O:4][C:2]2=[O:3].[NH2:13]C(N)=O.CN(C)C=O.N>CO.O>[NH:6]1[C:7]2[C:1](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:2](=[O:3])[NH:13][C:5]1=[O:4]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 1176UreaHCID 6228DimethylformamideHCID 8359Isatoic Anhydride

Product 1

HCID 64048QuinazolinedioneYield 76.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

978 g of isatoic acid anhydride were added in portions with stirring at 150° C. to a mixture of 720 g of urea and 1 liter of dimethylformamide and the mixture was then heated at 180° C. until evolution of ammonia ceased. The mixture was cooled and one liter of water was immediately added thereto followed by the addition of one liter of methanol. The warm mixture was stirred for one hour and was then filtered. The product was rinsed with warm water and with methanol and was then added with stirring to 2-3 volumes of warm dimethylformamide. The mixture was filtered and the product was rinsed with methanol to obtain 747 g of quinazoline-2,4-dione.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationwas then filtered
  3. washThe product was rinsed with warm water and with methanol
  4. additionwas then added
  5. stirringwith stirring to 2-3 volumes of warm dimethylformamide
  6. filtrationThe mixture was filtered
  7. washthe product was rinsed with methanol

Sources & evidence

ORD record
ord-2e4e4b665e384aa3a6b5acea03e9fdad
Source dataset
uspto-grants-1982_09
Patent number
US04350695

Reaction notes

Loading…