Reaktion #52243

Reaktionsgleichung

Ethanolamine

ethanol

3,6-Endoxo-1,2,3,6-tetrahydrophthalic anhydride

→

hydroxy ethylmaleimide

Lösungsmittel

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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,).

Quelle