Acetic Anhydride → Maleimide styrene

HRID 345918Notes

Reaction equation

HRID 345918 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]([OH:16])(=O)/[CH:10]=[CH:11]\[C:12]([NH2:14])=[O:13].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>O>[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:12]1(=[O:13])[NH:14][C:9](=[O:16])[CH:10]=[CH:11]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 66721924HCID 66721924, compound

Product 1

HCID 66643759Maleimide styrene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.0 g of Styrene/maleamic acid and 0.5 g of anhydrous sodium acetate were added to 50 mL of acetic anhydride in a round bottom flask equipped with an inert gas inlet tube, magnetic stirrer and a heating bath. The resulting solution was heated and maintained at 80°-85° C. under nitrogen for 3 hr. The cooled solution was poured in a slow stream into a well stirred beaker of 400 ml cold (5°-10° C.) water. The resulting solid was collected by suction filtration, washed with four portions of acidic (1 mL acetic acid per 200 mL of water) ice water and vacuum dried. Nearly quantitative yields of product were obtained.

Workup

  1. customequipped with an inert gas inlet tube, magnetic stirrer and a heating bath
  2. temperatureThe resulting solution was heated
  3. temperaturemaintained at 80°-85° C. under nitrogen for 3 hr
  4. filtrationThe resulting solid was collected by suction filtration
  5. washwashed with four portions of acidic (1 mL acetic acid per 200 mL of water) ice water and vacuum
  6. customdried
  7. customNearly quantitative yields of product
  8. customwere obtained

Sources & evidence

ORD record
ord-1d502836fe844b8baf2b2b5594811b36
Source dataset
uspto-grants-1991_10
Patent number
US05059513

Reaction notes

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