Acetic Anhydride → 4-phenylmorpholine-2,6-dione

HRID 2220016Notes

Reaction equation

HRID 2220016 reaction equation
[C:1]1([N:7]([CH2:12][C:13]([OH:15])=[O:14])[CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OC(=O)C)(=O)C.CCCCCC>C1(C)C=CC=CC=1>[C:1]1([N:7]2[CH2:8][C:9](=[O:11])[O:15][C:13](=[O:14])[CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8058HexaneHCID 136915N-Phenyliminodiacetic acid (anhydride)

Product 1

HCID 5632194-phenylmorpholine-2,6-dioneYield 90.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 2-liter eggplant type flask, 62.8 g of N-phenyl-iminodiacetic acid was charged and dissolved in 500 mL of toluene under a nitrogen gas stream, to which was then added 32.0 g of acetic anhydride. The mixture was refluxed under heating and stirred. One hour thereafter, the reaction mixture was cooled to room temperature, to which was then 3 L of hexane with stirring to undergo deposition. A reaction product was filtered to obtain 52.0 g of N-phenyliminodiacetic anhydride.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating
  3. filtrationA reaction product was filtered

Sources & evidence

ORD record
ord-41a59fd57fb94fa19ccf6d05578f4513
Source dataset
uspto-grants-2008_08
Patent number
US07416835B2

Reaction notes

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