Propionic anhydride → HCID 69111590, compound

HRID 1791883Notes

Reaction equation

HRID 1791883 reaction equation
[OH:1][C:2]1[CH:13]=[C:6]2[C:7]([O:9][C:10](=[O:12])[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8].[CH3:14][O-].[Na+].[C:17](OC(=O)CC)(=O)[CH2:18]C>CO>[CH3:14][O:9][C:7](=[O:8])[C:6]1[CH:13]=[C:2]([OH:1])[CH:3]=[CH:4][C:5]=1[NH:11][C:10](=[O:12])[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 31263Propionic anhydrideHCID 27593156-hydroxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneHCID 10942334Sodium Methoxide

Product 1

HCID 69111590HCID 69111590, compoundYield 680%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Hydroxy isatoic anhydride (17.9 g, 0.1 mol) was heated to reflux with sodium methoxide (0.5 g, 0.01 mol) in methanol (600 mL) for 1 h. The reaction mixture was cooled on icebath, propionic anhydride (15.0 g, 0.115 mol) was added and then the mixture was heated to reflux for 0.5 h The mixture was then concentrated under reduced pressure to app. one-half of its original volume and left over night in a refrigerator. The resulting precipitate was collected, washed with methanol and dried to give the title compound as pure white crystals (15.2 g, 0.068 mol).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 0.5 h The mixture
  4. concentrationwas then concentrated under reduced pressure
  5. waitone-half of its original volume and left over night in a refrigerator
  6. customThe resulting precipitate was collected
  7. washwashed with methanol
  8. customdried

Sources & evidence

ORD record
ord-2087ff8c32ec4f379e147c94479483ad
Source dataset
uspto-grants-2006_07
Patent number
US07074831B2

Reaction notes

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