Реакция #927980

Уравнение реакции

Ethanolamine

ethanol

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

→

hydroxy ethylmaleimide

Растворители

Условия реакции

Обработка

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

Методика

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,).

Источник