Sodium Hydroxide → HCID 136388401, compound

HRID 2082951Notes

Reaction equation

HRID 2082951 reaction equation
[NH2:1][C:2]1[NH:3][C:4]([C:9]#[N:10])=[C:5]([C:7]#[N:8])[N:6]=1.N([O-])=O.[Na+].[N+:15](=[C:17]1[N:21]=[C:20]([C:22]#[N:23])[C:19]([C:24]#[N:25])=[N:18]1)=[N-].S([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>O>[N:15]([C:17]1[NH:18][C:19]([C:24]#[N:25])=[C:20]([C:22]#[N:23])[N:21]=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 14798Sodium HydroxideHCID 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

5.34 g (40 mmol) of 2-amino-4,5-dicyanoimidazole was dissolved in 130 ml water plus 30 ml conc. hyrdrochloric acid and diazotized by the slow addition (over 5 min) of a solution of 4.0 g of sodium nitrite in 15 ml of water. The mixture was then stirred and cooled to 0°-10° for 45 minutes. The resulting cold suspension of 2-diazo-4,5-dicyanoimidazole was poured into a stirred solution of 12.4 g of sodium sulfite and 2.2 g of sodium hydroxide in 50 ml of water at 0°. An immediate yellow precipitate formed. The mixture was stirred at 0° for 30 minutes and then the yellow solid was filtered and air dried. This gave 0.85 g of 2,2'-azobis(4,5-imidazoledicarbonitrile). Recrystallization from water gave golden plates. UV(CH3CN): 390 nm, k 90.0; sh 375 nm, k 83.4; 237 nm, k 41.3).

Workup

  1. temperaturecooled to 0°-10° for 45 minutes
  2. customAn immediate yellow precipitate formed
  3. stirringThe mixture was stirred at 0° for 30 minutes
  4. filtrationthe yellow solid was filtered
  5. customair dried
  6. customRecrystallization from water
  7. customgave golden plates

Sources & evidence

ORD record
ord-e599a855266840ef84133aa3cf6c40e8
Source dataset
uspto-grants-1978_04
Patent number
US04083843

Reaction notes

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