Itaconic acid → N-Octyl-2-methyl-3-[3-(4-carboxy-2-oxo-pyrrolidino)phenyl]propenamide

HRID 66796

Reaktionsgleichung

Reaktionsgleichung von HRID 66796
[CH2:1]([NH:9][C:10](=[O:21])[C:11]([CH3:20])=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:22]([OH:30])(=[O:29])[C:23]([CH2:25][C:26](O)=[O:27])=[CH2:24]>C(OCC)(=O)C>[CH2:1]([NH:9][C:10](=[O:21])[C:11]([CH3:20])=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N:19]2[CH2:24][CH:23]([C:22]([OH:30])=[O:29])[CH2:25][C:26]2=[O:27])[CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Komponenten

4

Edukt 2

HCID 811Itaconic acidHCID 54067388N-octyl-2-methyl-3-(3-aminophenyl)propenamide

Produkt 1

HCID 53888869N-Octyl-2-methyl-3-[3-(4-carboxy-2-oxo-pyrrolidino)phenyl]propenamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4.3 g. of N-octyl-2-methyl-3-(3-aminophenyl)propenamide and 2.0 g. of itaconic acid was heated at ca. 140° C. for 1.25 hours. The reaction mixture was allowed to cool somewhat and then a small volume of ethyl acetate was added. This gave a clear solution. The solution was diluted to ca. 75 ml. with further ethyl acetate, and then it was extracted with 1 N potassium hydroxide. The potassium hydroxide solution was washed with ethyl acetate and then it was acidified using concentrated hydrochloric acid. This caused a gum to precipitate. The gum was extracted into ethyl acetate, and the ethyl acetate solution was dried using sodium sulfate. The dried solution was evaporated in vacuo to give 4.5 g. of an oil. The oil was triturated under ether causing formation of a solid. The solid was collected by filtration to give 2.5 g. of a solid, which was recrystallized from ethyl acetate-cyclohexane and then from acetonitrile. This afforded 1.3 g. of the title compound, m.p. 120°-121° C.

Aufarbeitung

  1. additionA mixture of 4.3 g
  2. temperatureto cool somewhat
  3. customThis gave a clear solution
  4. additionThe solution was diluted to ca. 75 ml
  5. extractionwith further ethyl acetate, and then it was extracted with 1 N potassium hydroxide
  6. washThe potassium hydroxide solution was washed with ethyl acetate
  7. customto precipitate
  8. extractionThe gum was extracted into ethyl acetate
  9. dry with materialthe ethyl acetate solution was dried
  10. customThe dried solution was evaporated in vacuo
  11. customto give 4.5 g
  12. customThe oil was triturated under ether causing formation of a solid
  13. filtrationThe solid was collected by filtration
  14. customto give 2.5 g
  15. customof a solid, which was recrystallized from ethyl acetate-cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-a7d2fdf805064a93852557762ef34b37
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04343813

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