Maleic Anhydride → HCID 86738052, compound

HRID 848556Notes

Reaction equation

HRID 848556 reaction equation
[CH3:1][CH:2]([NH:12][C:13](=[O:24])[CH:14]=[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=1)[CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[C:25]1(=[O:31])[O:30][C:28](=[O:29])[CH:27]=[CH:26]1>C1(C)C=CC=CC=1>[CH3:1][CH:2]([NH:12][C:13](=[O:24])[CH:14]=[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:25](=[O:31])/[CH:26]=[CH:27]\[C:28]([OH:30])=[O:29])[CH:18]=1)[CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 54502184HCID 54502184, compound

Product 1

HCID 86738052HCID 86738052, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 1.0 g. of the N-(1-methyldecyl)-3-(3-aminophenyl)-2-butenamide from Preparation 28 in 25 ml. of toluene was heated on a steam bath, and then 0.32 g. of maleic anhydride was added in one portion. After 3 minutes, the reaction mixture was cooled and the solvent was removed by evaporation in vacuo. The residue was triturated under a mixture of petroleum ether and acetonitrile, and the resulting solid was recrystallized from acetonitrile. This afforded 0.68 g. of the title compound as a light yellow solid, m.p. 126°-128° C. The IR spectrum (KBr disc) showed absorptions at 3333, 2941, 1724, 1639, 1587 and 1563 cm-1. The NMR spectrum (DMSO-d6) showed absorptions at 0.81 (s, 3H), 0.91 (s, 3H), 1.17 (s, 16H), 2.02 (m, 3H), 3.58 (m, 1H), 5.90 (d, 1H), 6.38 (m, 2H), 7.26 (m, 6H) and 10.40 (s, 1H) ppm.

Workup

  1. temperaturethe reaction mixture was cooled
  2. customthe solvent was removed by evaporation in vacuo
  3. customThe residue was triturated under a mixture of petroleum ether and acetonitrile
  4. customthe resulting solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-3cb972ddb6754072ae5841a98762cb37
Source dataset
uspto-grants-1981_10
Patent number
US04296129

Reaction notes

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