Urea → 7-Bromo-6-fluoroquinazoline-2,4(1H,3H)-dione

HRID 2284397Notes

Reaction equation

HRID 2284397 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Br:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4](O)=[O:5].[NH2:13][C:14](N)=[O:15]>O>[Br:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:13][C:14](=[O:15])[NH:1]2)=[CH:7][C:8]=1[F:12]

Participants

4

Reactant 2

HCID 1176UreaHCID 675149612-Amino-4-bromo-5-fluorobenzoic acid

Product 1

HCID 675174657-Bromo-6-fluoroquinazoline-2,4(1H,3H)-dioneYield 51.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

To a 100 mL round bottom flask, 2-amino-4-bromo-5-fluoro-benzoic acid (0.7 g, 2.99 mmol) and urea (1.07 g, 17.94 mmol) were added. The reaction mixture was stirred at 200° C. for 2 hours. The reaction mixture was allowed to cool to 100° C. and water was added. The aqueous reaction mixture was refluxed for 5-10 minutes and cooled to room temperature to provide the precipitate. The solid was filtered and dried to afford the title compound (400 mg, 51%). This material was taken to the next step without further purification.

Workup

  1. temperatureto cool to 100° C.
  2. temperatureThe aqueous reaction mixture was refluxed for 5-10 minutes
  3. temperaturecooled to room temperature
  4. customto provide the precipitate
  5. filtrationThe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-208e306eb79944ebaf56cae83b09bdbb
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

Loading…