Acetic Anhydride → HCID 86584103, compound

HRID 277314Notes

Reaction equation

HRID 277314 reaction equation
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.C(O[C:12](=O)[CH3:13])(=O)C.[CH2:15]([N:17](CC)CC)C.C([O-])(=O)C.[Na+]>C(Cl)(Cl)Cl>[CH2:1]=[CH:2][CH:3]=[CH2:4].[C:1]1(=[O:7])[NH:17][C:4](=[O:5])[CH:3]=[CH:2]1.[C:1]1(=[O:7])[NH:17][C:4](=[O:5])[CH:3]=[CH:2]1.[C:15](#[N:17])[CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 8471TriethylamineHCID 517045Sodium Acetate

Product 1

HCID 86584103HCID 86584103, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Amino-terminated butadiene-acrylonitrile (sold as Hycar resin 1300 X42 ATBN by BF Goodrich, in which the m and n depicted in the structure are integers to provide a number average molecular weight of 3600) (450 g, 500 mmol based on amine equivalent weight AEW=450 g) was dissolved in CHCl3 (1000 mL) in a 3 L four-necked flask equipped with addition funnel, mechanical stirrer, internal temperature probe and nitrogen inlet/outlet. The stirred solution was placed under nitrogen and cooled on an ice bath. The addition funnel was charged with maleic anhydride (98.1 g, 1 mol) in CHCl3 (50 mL) and this solution was added to the reaction over 30 minutes, maintaining the internal reaction temperature below 10° C. This mixture was stirred for 30 minutes on ice, then allowed to warm to room temperature and stirred for an additional 4 hours. To the resulting slurry was added acetic anhydride (Ac2O) (653.4 g, 6 mol), triethylamine (Et3N) (64.8 g, 0.64 mol) and sodium acetate (NaOAc) (62.3 g, 0.76 mol). The reaction was heated to mild reflux for 5 hours, allowed to cool to room temperature, and subsequently extracted with H2O (1 L), satd. NaHCO3 (1 L) and H2O (2×1 L). Solvent was removed in vacuo to yield the maleimide terminated butadiene acrylonitrile.

Workup

  1. customAmino-terminated butadiene-acrylonitrile (
  2. customto provide a number average molecular weight of 3600) (450 g, 500 mmol based on amine equivalent weight AEW=450 g)
  3. customequipped with addition funnel, mechanical stirrer
  4. temperaturecooled on an ice bath
  5. additionthis solution was added to the reaction over 30 minutes
  6. temperaturemaintaining the internal reaction temperature below 10° C
  7. stirringstirred for an additional 4 hours
  8. temperatureThe reaction was heated
  9. temperatureto mild reflux for 5 hours
  10. temperatureto cool to room temperature
  11. extractionsubsequently extracted with H2O (1 L)
  12. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-5b02173dc231431d9bca5d8434c30e12
Source dataset
uspto-grants-2002_03
Patent number
US06355750B1

Reaction notes

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