Acetic Acid → 7-Fluoroquinazoline-2,4(1H,3H)-dione

HRID 927297Notes

Reaction equation

HRID 927297 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].[O-:12][C:13]#[N:14].[K+].C(O)(=O)C.[OH-].[Na+]>O>[F:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:14][C:13](=[O:12])[NH:1]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 27249674-Fluoroanthranilic acidHCID 11378442Potassium cyanate

Product 1

HCID 126665257-Fluoroquinazoline-2,4(1H,3H)-dioneYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-amino-4-fluorobenzoic acid (4.0 g, 26 mmol) and potassium cyanate (3.5 g, 43 mmol) in water (200 mL) was added acetic acid (3 mL, 45 mmol) and the mixture was stirred at room temperature for about 5 h. To the mixture was added NaOH (15 g, 375 mmol) and it was stirred for another 1 h. The mixture was filtered and the solid was mixed in hot water, and it was adjusted to pH=5˜6 by addition of acetic acid. The mixture was filtered and washed with water, dried to give the title compound (3.0 g, 65% yield) as gray solid. MS: m/z 181.1 [M+H]+

Workup

  1. stirringwas stirred for another 1 h
  2. filtrationThe mixture was filtered
  3. additionthe solid was mixed in hot water
  4. additionit was adjusted to pH=5˜6 by addition of acetic acid
  5. filtrationThe mixture was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-52162d0877b54bd6b58f0375ab64a47a
Source dataset
uspto-grants-2016_03
Patent number
US09290460B2

Reaction notes

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