Ethylenediamine → 9H-carbazole-3,6-dicarbonitrile

HRID 460873Notes

Reaction equation

HRID 460873 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10](Br)=[CH:9][CH:8]=3.C(N)[CH2:17][NH2:18].[CH3:20][N:21](C)C=O>>[C:17]([C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([C:20]#[N:21])=[CH:9][CH:8]=3)#[N:18]

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 6228DimethylformamideHCID 2748743,6-Dibromocarbazole

Product 1

HCID 107751409H-carbazole-3,6-dicarbonitrile

Procedure

A slurry of 3,6-dibromocarbazole (33.3 g) and cuprous cyanide (39 g) in 50 ml of dimethylformamide is heated at 160° C for seven days. The reaction mixture is poured into 1 liter of aqueous ethylenediamine (20%, v/v) and the mixture is stirred for fifteen minutes and filtered. The precipitate is slurried in 1 liter of aqueous ethylenediamine (20%, v/v) and stirred for about 16 hours. The precipitate is collected by filtration and recrystallized from dimethylformamide to yield 15 g of 3,6-dicyanocarbazole, melting point 360° C.

Workup

  1. filtrationfiltered
  2. stirringstirred for about 16 hours
  3. filtrationThe precipitate is collected by filtration
  4. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-a5d46d8d7a8b4ab99e551835dd34d97e
Source dataset
uspto-grants-1977_12
Patent number
US04061655

Reaction notes

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