Toluene → 4-phenylmorpholine-2,6-dione

HRID 729216Notes

Reaction equation

HRID 729216 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.C1(C)C=CC=CC=1.C(OC(=O)C)(=O)C>CCCCCC>[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 1140TolueneHCID 7918Acetic AnhydrideHCID 136915N-Phenyliminodiacetic acid (anhydride)

Product 1

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

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Into a 2-liter round-bottom flask was put 62.8 g of N-phenyliminodiacetic acid under nitrogen gas stream to dissolve with 500 ml of toluene. To the solution was added 32.0 g of acetic anhydride, and the mixture was refluxed by heating with stirring. After lapse of one our, the mixture was cooled to room temperature and 3 liters of hexane was added thereto with stirring to deposit. The deposit was collected by filtration to obtain 52.0 g of N-phenyliminodiacetic acid anhydride.

Workup

  1. customInto a 2-liter round-bottom flask was put
  2. temperaturethe mixture was refluxed
  3. temperatureby heating
  4. stirringwith stirring to deposit
  5. filtrationThe deposit was collected by filtration

Sources & evidence

ORD record
ord-29e3ef4f978547f0abe8c753ae9dfcc2
Source dataset
uspto-grants-2009_09
Patent number
US07582410B2

Reaction notes

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