Reaktion #52246

ord-5f717293ced543b9a3f0f746b5bde313

Reaktionsgleichung

O=C([O-])[O-].[K+].[K+]
K2CO3
O=C1C=CC(=O)O1
Maleic anhydride
NCCO
ethanolamine
CC(=O)OC(C)=O
acetic anhydride
CC(=O)[O-].[Na+]
sodium acetate
→
CC(=O)OCCC1=CC(=O)NC1=O
Acetoxy Ethyl Maleimide

Edukte

—
ice water
O=C([O-])[O-].[K+].[K+]
K2CO3
O=C1C=CC(=O)O1
Maleic anhydride
NCCO
ethanolamine
CC(=O)OC(C)=O
acetic anhydride
CC(=O)[O-].[Na+]
sodium acetate

Reagenzien

Keine

Lösungsmittel

CC(C)=O
acetone
CC(=O)O
acetic acid

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe solution was heated to 80 C
  2. 2
    workup.STIRRINGstirred for 1 hour
  3. 3
    ExtraktionThe product was extracted with methylene chloride
  4. 4
    Sonstigedried
  5. 5
    SonstigeThe product was purified by sublimation
  6. 6
    Sonstigeyielding white crystals, m.p. 76° C. (44.1 g, 13.45%)

Vorschrift

Maleic anhydride (172.32 g, 1.75 mol) was added to ethanolamine (107.34 g, 1.75 mol) and dissolved in 500 mL of acetone while stirring overnight in an ice bath. To the solution, 400 mL of acetic anhydride (4.23 mol) was added with sodium acetate (144 g, 1.75 mol). The solution was heated to 80 C and stirred for 1 hour. The contents were poured into ice water and the acetic acid neutralized with K2CO3. The product was extracted with methylene chloride and then dried using magnesium sulfate. The product was purified by sublimation yielding white crystals, m.p. 76° C. (44.1 g, 13.45%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06855745B2uspto-grants-2005_02