Acetic Acid → 6-iodo-1H-quinazoline-2,4-dione

HRID 1648220

Reaction equation

HRID 1648220 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4](O)=[O:5].C(O)(=O)C.[O-:16][C:17]#[N:18].[K+].[OH-].[Na+]>O.C1COCC1>[I:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[NH:1][C:17](=[O:16])[NH:18][C:4]2=[O:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 72911Benzoic acid, 2-amino-5-iodo-HCID 11378442Potassium cyanate2×

Product 1

HCID 113806686-iodo-1H-quinazoline-2,4-dioneYield 91.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 25.36 g of 2-amino-5-iodobenzoic acid in 250 ml of water and 90 mL of THF was added 7.40 g of glacial acetic acid and stirred at room temperature. Then was added 7.82 g of potassium cyanate in water dropwise. Left to overnight. Added another 5.47 g of potassium cyanate. Stirred overnight. A total of 160 g of NaOH pellets were added portionwise, keeping the mixture cool in ice-water bath. The mixture was stirred at room temperature overnight. The mixture was cooled in a refrigerator and the precipitate filtered through a sintered glass funnel. The precipitate was then dissolved in water and acidified with 4N HCl. The precipitate was collected by filtration. The solid was dried in a vacuum oven to yield 25.44 g of the title compound.

Workup

  1. stirringStirred overnight
  2. stirringThe mixture was stirred at room temperature overnight
  3. temperatureThe mixture was cooled in a refrigerator
  4. filtrationthe precipitate filtered through a sintered glass funnel
  5. dissolutionThe precipitate was then dissolved in water
  6. filtrationThe precipitate was collected by filtration
  7. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-318027e0e75040bdb499c40da42c5e2a
Source dataset
uspto-grants-1995_07
Patent number
US05436233

Linked notes

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