N,N-Dimethylethylenediamine → HCID 19808700, compound

HRID 374040Notes

Reaction equation

HRID 374040 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:18](=O)[O:17][C:15](=[O:16])[C:5]2=[C:6]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][C:7]=12.[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][NH2:24]>C1(C)C=CC=CC=1>[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][N:24]1[C:15](=[O:16])[C:5]2[C:6]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[O:8][C:7]=3[C:2]([CH3:1])=[CH:3][C:4]=2[C:18]1=[O:17]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 12223605HCID 12223605, compound

Product 1

HCID 19808700HCID 19808700, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 50 ml of toluene were added 140 mg of 4-methyldibenzofuran-1,2-dicarboxylic anhydride and 270 mg of N,N-dimethylethylenediamine. The mixture was azeotropicallyl refluxed for 2 hours. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from ethanol to obtain 160 mg (yield: 89%) of 2-(2-dimethylaminoethyl)-5-methyl-1H-benzofuro[3,2-e]isoindole-1,3(2H)-dione as light yellow needles.

Workup

  1. temperatureThe mixture was azeotropicallyl refluxed for 2 hours
  2. customThe solvent was removed by distillation under reduced pressure
  3. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-033b9bc9d7f24408b95c7e5fea876dc8
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

Loading…