Maleic Anhydride → HCID 86738052, compound

HRID 1065805Notes

Reaction equation

HRID 1065805 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 27 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 a few minutes the reaction mixture was cooled and the toluene was removed by evaporation in vacuo. The residue was recrystallized from acetonitrile to give 0.70 g. of the title compound as a white solid, m.p. 79°-78° C. (dec.). The IR spectrum (KBr disc) showed absorptions at 3448, 3279, 2941, 1724, 1639, 1587 and 1563 cm-1. The NMR spectrum (DMSO-d6) showed absorptions at 0.9 (m, 3H), 1.09 (m, 3H), 1.26 (s, 16H), 2.47 (m, 3H, under DMSO-d6), 3.8 (m, 1H), 6.26 (m, 3H), 7.62 (m, 6H) and 10.44 (s, 1H) ppm.

Workup

  1. temperatureAfter a few minutes the reaction mixture was cooled
  2. customthe toluene was removed by evaporation in vacuo
  3. customThe residue was recrystallized from acetonitrile
  4. customto give 0.70 g

Sources & evidence

ORD record
ord-14f985242c2c4d4ab44449d849016c63
Source dataset
uspto-grants-1982_05
Patent number
US04331683

Reaction notes

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