Ethanolamine → HCID 66629678, compound

HRID 243745Notes

Reaction equation

HRID 243745 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 66629678HCID 66629678, compound

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-4c989282a5e84c9c815fa8ea260e55f2
Source dataset
uspto-grants-2014_02
Patent number
US08653286B2

Reaction notes

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