Ethanolamine → Hydroxy ethylmaleimide

HRID 1636467Notes

Reaction equation

HRID 1636467 reaction equation
[CH2:1]([CH2:3][NH2:4])O.C1[CH:10]2[O:11]C([CH:8]3[C:15](=O)[O:14]C(=O)[CH:9]32)C=1.C([OH:19])C>>[OH:14][CH2:15][CH2:8][C:9]1[C:10]([NH:4][C:3](=[O:19])[CH:1]=1)=[O:11]

Participants

4

Reactant 3

HCID 700EthanolamineHCID 702EthanolHCID 984843a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione

Product 1

HCID 22337974Hydroxy ethylmaleimide

Conditions

Temperature
0 °C

Procedure

Ethanolamine (80.96 g, 1.32 mol) was added to 500 mL of ethanol and cooled to 0° C. using an ice bath. 3,6-Endoxo-1,2,3,6-tetrahydrophthalic anhydride (220.21 g, 1.32 mol) was added to the solution and allowed to stir overnight. The yellow tinted crystals were used without purification. The solution was refluxed for four hours with azeotropic removal of water. The solution was cooled to 0° C. and the resulting crystals filtered (151.74 g, 54.95%). Removal of furan was facilitated by refluxing the crystals in xylenes for 4 hours with quantitative yield of hydroxy ethylmaleimide after purification by sublimation to yield white crystals, --CH2O--), 134.2 (2C, --CH=CH--), 171.2 (2C, --NC=O m.p. 68° C. 1H-NMR (CDCl3, δ, ppm): 2.62 (1H, --OH, s), 3.82-3.77 (4H, --NCH2CH2O--, overlapping), 6.76 (2H, --CH=CH--, s). 13C-NMR (CDCl3, δ, ppm): 40.5 (1C, --NCH2 --), 60.5 (1C,).

Workup

  1. customThe yellow tinted crystals were used without purification
  2. temperatureThe solution was refluxed for four hours with azeotropic removal of water
  3. temperatureThe solution was cooled to 0° C.
  4. filtrationthe resulting crystals filtered (151.74 g, 54.95%)
  5. customRemoval of furan

Sources & evidence

ORD record
ord-f86725a820934552a9045035411409b5
Source dataset
uspto-grants-2000_03
Patent number
US06034150

Reaction notes

Loading…