Urea → 6,7,8-Trimethoxyquinazoline-2,4(1H,3H)-dione

HRID 344712Notes

Reaction equation

HRID 344712 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[C:5]([C:6]([OH:8])=O)[C:4]=1[NH2:16].[NH2:17][C:18](N)=[O:19]>O>[CH3:15][O:14][C:10]1[CH:9]=[C:5]2[C:4](=[C:3]([O:2][CH3:1])[C:11]=1[O:12][CH3:13])[NH:16][C:18](=[O:19])[NH:17][C:6]2=[O:8]

Participants

4

Reactant 2

HCID 1176UreaHCID 966023,4,5-Trimethoxyanthranilic acid

Product 1

HCID 57434216,7,8-Trimethoxyquinazoline-2,4(1H,3H)-dioneYield 45.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 4.94 g (21.7 mmols) of 3,4,5-trimethoxyanthranilic acid and 15.15 g (249.8 mmols) of urea was heated at 145° C for an hour with stirring. After cooling, water was added and the mixture was heated at the boiling point with stirring. The solid was taken out by filtration and dried to afford 2.47 g (yield: 45%) of 6,7,8-trimethoxyquinazoline-2,4-dione.

Workup

  1. temperatureAfter cooling
  2. temperaturethe mixture was heated at the boiling point
  3. stirringwith stirring
  4. filtrationThe solid was taken out by filtration
  5. customdried

Sources & evidence

ORD record
ord-a2fb4af130ef44948c9087476214cf59
Source dataset
uspto-grants-1991_10
Patent number
US05053408

Reaction notes

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