Urea → 7-Bromoquinazoline-2,4(1H,3H)-dione

HRID 517437Notes

Reaction equation

HRID 517437 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[NH2:12][C:13](N)=[O:14]>O>[Br:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:12][C:13](=[O:14])[NH:1]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 886912-Amino-4-bromobenzoic acid

Product 1

HCID 140563807-Bromoquinazoline-2,4(1H,3H)-dioneYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
195 °C

Procedure

To a 250 mL round bottom flask, 2-amino-4-bromo-benzoic acid (10 g, 0.0463 mol) and urea (27.78 g, 0.4629 mol) were added. The reaction mixture was stirred at 195° C. for 3 h. The reaction mixture was allowed to reach 80° C. and water was added. The aqueous reaction mixture was stirred at 80° C. for 5-10 min then allowed to reach room temperature. The solid was filtered, dried and azeotroped with toluene to afford the title compound [10 g, 90%]. This material was taken to the next step without any further purification.

Workup

  1. customto reach 80° C.
  2. stirringThe aqueous reaction mixture was stirred at 80° C. for 5-10 min
  3. customto reach room temperature
  4. filtrationThe solid was filtered
  5. customdried
  6. customazeotroped with toluene

Sources & evidence

ORD record
ord-152576ca64704c7aaca76dae3d463079
Source dataset
uspto-grants-2015_08
Patent number
US09115092B2

Reaction notes

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