N,N-Dimethylethylenediamine → N-(2-dimethylaminoethyl)-carbazole-3,4-dicarboximide

HRID 374022Notes

Reaction equation

HRID 374022 reaction equation
C([N:4]1[C:16]2[CH:15]=[CH:14][C:13]3[C:17]([O:19][C:20](=[O:21])[C:12]=3[C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)=O)(=O)C.[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH2:26]>C1(C)C=CC=CC=1>[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][N:26]1[C:20](=[O:21])[C:12]2[C:11]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[NH:4][C:16]=3[CH:15]=[CH:14][C:13]=2[C:17]1=[O:19]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 183667359-Acetylcarbazole-3,4-dicarboxylic anhydride

Product 1

HCID 19808710N-(2-dimethylaminoethyl)-carbazole-3,4-dicarboximideYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 100 ml of toluene were added 1.12 g of 9-acetylcarbazole-3,4-dicarboxylic anhydride and 1.06 g of N,N-dimethylethylenediamine. The mixture was azeotropically refluxed for 2 hours. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from n-propanol to obtain 960 mg (yield: 78%) of N-(2-dimethylaminoethyl)-carbazole-3,4-dicarboximide as light yellow needles.

Workup

  1. temperatureThe mixture was azeotropically refluxed for 2 hours
  2. customThe solvent was removed by distillation under reduced pressure
  3. customThe residue was recrystallized from n-propanol

Sources & evidence

ORD record
ord-2c6c810a367e4dcaa3ffde9f1b62f8a7
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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