Acetic Acid → 5-methoxy-3-methyl-1H-quinazoline-2,4-dione

HRID 598071Notes

Reaction equation

HRID 598071 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([NH:16][CH3:17])=[O:15])[C:4]=1[C:5](NC)=[O:6].[OH-].[Na+].C(O)(=O)C>O.C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:6])[N:16]([CH3:17])[C:14](=[O:15])[NH:13]2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 672680242-Methoxy-N-methyl-6-[[(methylamino)carbonyl]amino]benzamide

Product 1

HCID 672670575-methoxy-3-methyl-1H-quinazoline-2,4-dioneYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-Methoxy-N-methyl-6-[[(methylamino)carbonyl]amino]benzamide (200 mg, 0.843 mmol), 5% sodium hydroxide solution in water (8 ml) and ethanol (4 ml) was refluxed for 1 h. The solution was allowed to cool and then acidified with acetic acid. The aqueous solution was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under vacuum to afford 168 mg (97%) of the title compound.

Workup

  1. temperaturewas refluxed for 1 h
  2. temperatureto cool
  3. extractionThe aqueous solution was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7be018ffceb44458a5f7a83ce0c4a6e1
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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