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

HRID 66795

Reaction equation

HRID 66795 reaction equation
[CH2:1]([NH:11][C:12](=[O:22])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:23]([OH:31])(=[O:30])[C:24]([CH2:26][C:27](O)=[O:28])=[CH2:25]>C(OCC)(=O)C>[CH2:1]([NH:11][C:12](=[O:22])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]2[CH2:25][CH:24]([C:23]([OH:31])=[O:30])[CH2:26][C:27]2=[O:28])[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 811Itaconic acidHCID 53861940N-decyl-3-(3-aminophenyl)propenamide

Product 1

HCID 53878346N-Decyl-3-[3-(4-carboxy-2-oxo-pyrrolidino)phenyl]propenamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9.0 g. of N-decyl-3-(3-aminophenyl)propenamide and 3.9 g. of itaconic acid was heated as a melt at 140°-145° C. for 1 hour, and then ca. 70 ml. of ethyl acetate was added to the hot mass. The resulting mixture was stirred, and a solid appeared. The mixture was cooled to room temperature, and the solid was recovered by filtration to give 9.5 g. of the title compound. This product was recrystallized from acetonitrile to give 8.4 g. (69% yield) of product having a melting point of 152.5°-153.5° C.

Workup

  1. additionA mixture of 9.0 g
  2. filtrationthe solid was recovered by filtration
  3. customto give 9.5 g

Sources & evidence

ORD record
ord-5db9f24c72b74b83ad7151b3a67c7621
Source dataset
uspto-grants-1982_08
Patent number
US04343813

Linked notes

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