Ethanolamine → 2-Hydroxyethylmaleimide Furan

HRID 2382217Notes

Reaction equation

HRID 2382217 reaction equation
C1[CH:6]2[O:7][CH:3]([CH:4]3[C:11](=O)[O:10]C(=O)[CH:5]32)C=1.[CH2:13]([CH2:15][NH2:16])O.C([OH:19])C>>[OH:10][CH2:11][CH2:4][C:5]1[C:6]([NH:16][C:15](=[O:19])[CH:13]=1)=[O:7].[O:7]1[CH:3]=[CH:4][CH:5]=[CH:6]1

Participants

4

Reactant 3

HCID 700EthanolamineHCID 702Ethanol2×HCID 984843a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione

Product 1

HCID 666296782-Hydroxyethylmaleimide Furan

Procedure

To a solution of exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (Sigma-Aldrich, St. Louis Mo.; 30.0 g, 0.181 moles) in anhydrous ethyl alcohol (40 mL), a solution of ethanolamine (12.6 g, 0.206 moles) in anhydrous ethyl alcohol (10 mL) was added over a time period of 2 hours to form a mixture. The mixture was then refluxed for about 3.5 hours and was cooled to room temperature and left to stand overnight. The precipitated product that formed during overnight standing was filtered off and washed with 20 mL of anhydrous ethyl alcohol. The collected solid was then dried under reduced pressure giving 18.3 g of white crystals. NMR (d6-DMSO): 2.92 ppm (s, —CH, 2H), 3.41 ppm (m, —CH2CH2—, 4H), 4.77 ppm (bm, —OH, 1H), 5.12 ppm (s, —CH, 2H), 6.55 ppm (s, —CH═CH—, 2H). Purity: ˜100%.

Workup

  1. customto form a mixture
  2. temperatureThe mixture was then refluxed for about 3.5 hours
  3. waitleft
  4. customThe precipitated product that formed during overnight
  5. filtrationstanding was filtered off
  6. washwashed with 20 mL of anhydrous ethyl alcohol
  7. customThe collected solid was then dried under reduced pressure

Sources & evidence

ORD record
ord-bb7d62d390fd4796b0c367c685c2a218
Source dataset
uspto-grants-2012_09
Patent number
US08258324B2

Reaction notes

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