Ethanolamine → Hydroxy ethylmaleimide

HRID 840798

반응식

HRID 840798 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

HCID 22337974Hydroxy ethylmaleimide

반응 조건

온도
0 °C

실험 절차

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,).

후처리

  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

출처 및 근거

ORD 기록
ord-774f72b8b8da4eb9a4b4a563883888d7
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06369124B1

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