Ethanolamine → 2-Hydroxyethylmaleimide Furan

HRID 1711811노트

반응식

HRID 1711811 반응식
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

참가 물질

4

반응물 3

HCID 700EthanolamineHCID 702Ethanol2회HCID 984843a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione

생성물 1

HCID 666296782-Hydroxyethylmaleimide Furan

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-d8059857b70f427987027430305d304c
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790835B2

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