Cyanogen Chloride → 1H-Imidazole-4,5-dicarbonitrile, 2-amino-

HRID 2082401Notes

Reaction equation

HRID 2082401 reaction equation
[NH2:1]/[C:2](/[C:7]#[N:8])=[C:3](\[NH2:6])/[C:4]#[N:5].[N:9]#[C:10]Cl>O1CCCC1>[NH2:9][C:10]1[NH:1][C:2]([C:7]#[N:8])=[C:3]([C:4]#[N:5])[N:6]=1

Participants

4

Reactant 2

HCID 10477Cyanogen ChlorideHCID 2723951Diaminomaleonitrile

Product 1

HCID 1704461H-Imidazole-4,5-dicarbonitrile, 2-amino-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diaminomaleonitrile (26.2 g) was added in portions to a solution containing cyanogen chloride (14.9 g) in tetrahydrofuran (200 ml). The mixture was then warmed to room temperature and finally heated under reflux for 1 hour. The resulting brown solid was collected by filtration and washed with a solution of sodium acetate. The remaining solid was dissolved in a sodium bicarbonate solution and treated with charcoal, filtered and acidified to give 2-amino-4,5-dicyanoimidazole, m.p. 276°-278°.

Workup

  1. temperaturefinally heated
  2. temperatureunder reflux for 1 hour
  3. filtrationThe resulting brown solid was collected by filtration
  4. washwashed with a solution of sodium acetate
  5. dissolutionThe remaining solid was dissolved in a sodium bicarbonate solution
  6. additiontreated with charcoal
  7. filtrationfiltered

Sources & evidence

ORD record
ord-90517b33383348b69cf31cbbc803dde1
Source dataset
uspto-grants-1993_02
Patent number
US05189053

Reaction notes

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