Acetic Acid → 6-Chloroquinazoline-2,4(1H,3H)-dione

HRID 45700

Reaction equation

HRID 45700 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4](O)=[O:5].C(O)(=O)C.[O:16]([C:18]#[N:19])[Na].[OH-].[Na+]>O>[Cl:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[NH:1][C:18](=[O:16])[NH:19][C:4]2=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 124762-Amino-5-chlorobenzoic acidHCID 14798Sodium HydroxideHCID 178418852HCID 178418852, compound

Product 1

HCID 3039986-Chloroquinazoline-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

Into a 500-mL 3-necked round-bottom flask, was placed a solution of 2-amino-5-chlorobenzoic acid (10 g, 58.48 mmol, 1.00 equiv) in water (100 mL), acetic acid (8 g, 133.33 mmol, 2.24 equiv). This was followed by the addition of NaOCN (8.2 g, 126.15 mmol, 2.13 equiv). The mixture was stirred for 30 mins at 30° C. To this was added sodium hydroxide (86 g, 2.15 mol, 37.00 equiv). The resulting solution was stirred overnight at 30° C. The solids were collected by filtration. The residue was dissolved in water. The pH value of the solution was adjusted to 7 with hydrogen chloride (12 mol/L). The solids were collected by filtration. This resulted in 5 g (44%) of 6-chloroquinazoline-2,4(1H,3H)-dione as a white solid.

Workup

  1. customInto a 500-mL 3-necked round-bottom flask, was placed
  2. stirringThe resulting solution was stirred overnight at 30° C
  3. filtrationThe solids were collected by filtration
  4. dissolutionThe residue was dissolved in water
  5. filtrationThe solids were collected by filtration
  6. customThis resulted in 5 g (44%) of 6-chloroquinazoline-2,4(1H,3H)-dione as a white solid

Sources & evidence

ORD record
ord-a0a831190e1f4b5e9848c1c3b2620b18
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Linked notes

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