Maleic Anhydride → N-Decyl-3-(3-[cis-3-carboxypropenamido]phenyl)propenamide

HRID 1065804Notes

Reaction equation

HRID 1065804 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]1(=[O:29])[O:28][C:26](=[O:27])[CH:25]=[CH:24]1>C1C=CC=CC=1>[CH2:1]([NH:11][C:12](=[O:22])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:23](=[O:29])/[CH:24]=[CH:25]\[C:26]([OH:28])=[O:27])[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 7923Maleic AnhydrideHCID 53861940N-decyl-3-(3-aminophenyl)propenamide

Product 1

HCID 86738051N-Decyl-3-(3-[cis-3-carboxypropenamido]phenyl)propenamideYield 92%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred mixture of 0.907 g. of N-decyl-3-(3-aminophenyl)propenamide and 25 ml. of benzene was heated on a steam bath until a solution was obtained. To this solution was then added 0.358 g. of maleic anhydride in one portion. In about 30 seconds a solid precipitated. The mixture was allowed to cool and then the solid was recovered by filtration. The solid was recrystallized from acetic acid, to give 1.1 g. (92% yield) of the title compound, melting point 187°-188° C. The IR spectrum (KBr disc) showed absorptions at 3279, 2899, 1724, 1653, 1626, 1587 and 1563 cm-1. The NMR spectrum (in DMSO-d6) showed absorptions at 0.91 (m, 3H), 1.24 (s, 16H), 3.18 (m, 2H), 6.50 (m, 4H), 7.42 (m, 4H), 8.11 (m, 2H) and 10.50 (s, 1H) ppm.

Workup

  1. additionA stirred mixture of 0.907 g
  2. customwas obtained
  3. additionTo this solution was then added 0.358 g
  4. customIn about 30 seconds a solid precipitated
  5. temperatureto cool
  6. filtrationthe solid was recovered by filtration
  7. customThe solid was recrystallized from acetic acid
  8. customto give 1.1 g

Sources & evidence

ORD record
ord-d5d6a6a4e4c744fc9caca75abfa1f4ff
Source dataset
uspto-grants-1982_05
Patent number
US04331683

Reaction notes

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