Reacción #52246

ord-5f717293ced543b9a3f0f746b5bde313

Ecuación de reacción

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

Reactantes

—
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

Reactivos

Ninguno

Disolventes

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

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe solution was heated to 80 C
  2. 2
    workup.STIRRINGstirred for 1 hour
  3. 3
    ExtracciónThe product was extracted with methylene chloride
  4. 4
    Otrodried
  5. 5
    OtroThe product was purified by sublimation
  6. 6
    Otroyielding white crystals, m.p. 76° C. (44.1 g, 13.45%)

Procedimiento

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%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06855745B2uspto-grants-2005_02