Urea → HCID 178518335, compound

HRID 1666649Notes

Reaction equation

HRID 1666649 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[NH2:12][C:13](N)=[O:14]>>[F:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4]([OH:5])=[N:12][C:13]([OH:14])=[N:1]2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 1176UreaHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 178518335HCID 178518335, compoundYield 89.5%

Conditions

Temperature
160 °C

Procedure

A mixture of 2-amino-4-fluorobenzoic acid (25.3 g) and urea (48.9 g) was gradually added to a flask heated at 160° C. and then heated to 245° C. over 30 min. Light yellow solids were precipitated. The reaction mixture was cooled to room temperature, then methanol (250 mL) was added to the reaction mixture, the mixture was heated to reflux for 30 min, the solids were washed and cooled to room temperature, and then the precipitated solids were collected by filtration. The resulting solids were washed again with methanol (300 mL) to obtain 7-fluoroquinazoline-2,4-diol (26.3 g).

Workup

  1. additionwas gradually added to a flask
  2. temperatureheated to 245° C. over 30 min
  3. customLight yellow solids were precipitated
  4. temperatureThe reaction mixture was cooled to room temperature
  5. additionmethanol (250 mL) was added to the reaction mixture
  6. temperaturethe mixture was heated
  7. temperatureto reflux for 30 min
  8. washthe solids were washed
  9. temperaturecooled to room temperature
  10. filtrationthe precipitated solids were collected by filtration
  11. washThe resulting solids were washed again with methanol (300 mL)

Sources & evidence

ORD record
ord-3bf46fc582ac446d9d8f0bbf9dab3bdc
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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