Ethanolamine → Hydroxy ethylmaleimide

HRID 23965

Reaction equation

HRID 23965 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-3710d84d2a0043e5b0414d16ae327ec5
Source dataset
uspto-grants-2005_02
Patent number
US06855745B2

Linked notes

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