Hydrochloric Acid → HCID 136388401, compound

HRID 2082952Notes

Reaction equation

HRID 2082952 reaction equation
[NH2:1][C:2]1[NH:3][C:4]([C:9]#[N:10])=[C:5]([C:7]#[N:8])[N:6]=1.Cl.N([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+].[N+:22](=[C:24]1[N:28]=[C:27]([C:29]#[N:30])[C:26]([C:31]#[N:32])=[N:25]1)=[N-]>O>[N:22]([C:24]1[NH:25][C:26]([C:31]#[N:32])=[C:27]([C:29]#[N:30])[N:28]=1)=[N:1][C:2]1[NH:3][C:4]([C:9]#[N:10])=[C:5]([C:7]#[N:8])[N:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24437Sodium SulfiteHCID 1704461H-Imidazole-4,5-dicarbonitrile, 2-amino-HCID 124092412-Diazo-2H-imidazole-4,5-dicarbonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 136388401HCID 136388401, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

In a glass reactor 7.98 g (60 mmol) 2-amino-4,5-dicyanoimidazole was dissolved in 200 ml water plus 45 ml conc. hydrochloric acid. At 0° the stirred solution was diazotized over ~ 10 minutes by the slow addition of 6.0 g sodium nitrite dissolved in 15 ml water. The mixture was stirred for 1 hour at 0° to insure complete reaction. Then 7.52 g (60 mmol) anhydrous sodium sulfite dissolved in ~40 ml of water was added at once to the vigorously stirred suspension of 2-diazo-4,5-dicyanoimidazole. The bright yellow mixture was stirred for 30 minutes at 0° and filtered. The yellow cake was washed with a little cold water and air dried. This procedure was repeated two more times giving a total of 15.4 g of crude material. The crude product was recrystallized from boiling water (~600 ml). The hot solution was filtered. The yellow filtrate deposited golden plates on cooling. The product was collected at 0°, washed with a little ice water and dried in a vacuum oven at 70°. This gave 9.6g (41%) of 2,2'-azobis(4,5-imidazoledicarbonitrile); mp >300°.

Workup

  1. customreaction
  2. additionwas added at
  3. stirringThe bright yellow mixture was stirred for 30 minutes at 0°
  4. filtrationfiltered
  5. washThe yellow cake was washed with a little cold water and air
  6. customdried

Sources & evidence

ORD record
ord-cc22c11d31324364ac483c004d8e9be9
Source dataset
uspto-grants-1978_04
Patent number
US04083843

Reaction notes

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