Maleimide, N-p-tolyl- → HCID 19808698, compound

HRID 374015Notes

Reaction equation

HRID 374015 reaction equation
[CH:1]([C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=1)=[CH2:2].[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:23](=[O:24])[CH:22]=[CH:21][C:20]2=[O:25])=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]2[C:23](=[O:24])[CH:22]3[CH:21]([CH2:2][CH:1]=[C:3]4[O:4][C:5]5[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=5[CH:7]43)[C:20]2=[O:25])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 15399Maleimide, N-p-tolyl-HCID 5889742-Vinylbenzofuran

Product 1

HCID 19808698HCID 19808698, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10 ml of toluene was added to a mixture of 0.40 g of 2-vinylbenzofuran and 0.52 g of N-(4-methylphenyl)maleimide. The mixture was refluxed for 3 hours. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene/ethyl acetate=50/1 to 20/1) to obtain 0.45 g (yield: 49%) of 2-(4-methylphenyl)-3a,4,10b,10c-tetrahydro-1H-benzofuro-[3,2-e]isoindole-1,3(2H)-dione as colorless crystals.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. customThe solvent was removed by distillation under reduced pressure
  3. customThe residue was purified by column chromatography (eluant: toluene/ethyl acetate=50/1 to 20/1)

Sources & evidence

ORD record
ord-2c333b2f445e4c30994bd31fab318042
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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