Acetone → HCID 10492615, compound

HRID 1603968Notes

Reaction equation

HRID 1603968 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].C[C:13]([CH3:15])=[O:14].[C:16](OC(=O)C)(=[O:18])[CH3:17].[C:23]([O-])(=[O:25])[CH3:24].[Na+]>O>[C:16]([O:11][C:4]1[CH:3]=[C:2]([N:1]2[C:23](=[O:25])[CH:24]=[CH:15][C:13]2=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 180Acetone2×HCID 46494-Aminosalicylic AcidHCID 7918Acetic AnhydrideHCID 517045Sodium Acetate

Product 1

HCID 10492615HCID 10492615, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
57 °C

Procedure

A 3-liter, three-neck round-bottom flask was charged with 76.5 g (0.5 mole) of 4-aminosalicylic acid in 400 ml of reagent acetone. The flask was flushed with nitrogen and sealed under a nitrogen balloon as stirring was started. A solution of 50 g (0.51) of maleic anhydride dissolved in 400 ml of reagent acetone was added to maintain the temperature at reflux (about 57° C.) with added heat for 1 hour, which gave a very thick pale green precipitate. The flask was then charged with 153 g of acetic anhydride and 9 g of sodium acetate and reflux was continued for an additional 11/2 to 2 hours. The acetone was stripped from the reaction mixture and 1-liter of distilled water added to wash the solid. The solid was suction-filtered and dried at 100° C. under 29 inches of Hg vacuum. The yield of brown solid was near quantitative and melted at 110-119° C. The 400 MHz proton NMR analysis showed maleimide and O-acetyl formation.

Workup

  1. customThe flask was flushed with nitrogen
  2. customsealed under a nitrogen balloon
  3. dissolutionA solution of 50 g (0.51) of maleic anhydride dissolved in 400 ml of reagent acetone
  4. additionwas added
  5. temperatureto maintain the temperature
  6. additionwith added
  7. temperatureheat for 1 hour
  8. customwhich gave a very thick pale green precipitate
  9. temperaturereflux
  10. custom2 to 2 hours
  11. additionadded
  12. washto wash the solid
  13. filtrationThe solid was suction-filtered
  14. customdried at 100° C. under 29 inches of Hg vacuum

Sources & evidence

ORD record
ord-df9d5a5e8e844033931dca2c4713554c
Source dataset
uspto-grants-1999_11
Patent number
US05990210

Reaction notes

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