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

HRID 66796

반응식

HRID 66796 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a7d2fdf805064a93852557762ef34b37
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04343813

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