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

HRID 848492Notes

Reaction equation

HRID 848492 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 produce 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-4e2b0e3f701b4bfb925002561a560f0f
Source dataset
uspto-grants-1981_10
Patent number
US04296120

Reaction notes

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