Acetic Acid → 5-Chloroquinazoline-2,4-diol

HRID 2296705Notes

Reaction equation

HRID 2296705 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:11])[C:7]=1[C:8](O)=[O:9].[OH-].[Na+].[O-:14][C:15]#[N:16].[Na+].C(O)(=O)C.Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:7]=1[C:8](=[O:9])[NH:16][C:15](=[O:14])[NH:11]2

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 750712-Amino-6-chlorobenzoic acidHCID 517096Sodium Cyanate

Product 1

HCID 3340215-Chloroquinazoline-2,4-diolYield 72.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 6-chloroanthranilic acid (1.72 g, 10 mmol) and NaOH (0.40 g, 10 mmol) in water (15 mL) was added sodium cyanate (0.72 g, 11 mmol), followed by acetic acid (0.66 g, 11 mmol). The solution was stirred for 9 h, and then acidified with conc. HCl. The precipitate was filtered off and washed with water. The wet solid was added to a solution of NaOH (8.0 g, 200 mmol) in water (60 mL) and stirred for 20 h. The precipitate was filtered off and suspended in water (80 mL), then heated to boiling and acidified with 50% H2SO4. The cooled mixture was filtered, the solid washed well with water and dried to give 5-chloroquinazolin-2,4-dione (1.42 g, 72%).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. stirringstirred for 20 h
  4. filtrationThe precipitate was filtered off
  5. temperatureheated
  6. filtrationThe cooled mixture was filtered
  7. washthe solid washed well with water
  8. customdried

Sources & evidence

ORD record
ord-6362e5534d684eeea0fd4930720a26aa
Source dataset
uspto-grants-2002_12
Patent number
US06489328B2

Reaction notes

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