Pyridine → HCID 20358860, compound

HRID 2082953Notes

Reaction equation

HRID 2082953 reaction equation
[N:1]([C:12]1[NH:13][C:14]([C:19]#[N:20])=[C:15]([C:17]#[N:18])[N:16]=1)=[N:2][C:3]1[NH:4][C:5]([C:10]#[N:11])=[C:6]([C:8]#[N:9])[N:7]=1.N1C=CC=CC=1>[Zn].C(O)(=O)C>[NH:2]([C:3]1[NH:7][C:6]([C:8]#[N:9])=[C:5]([C:10]#[N:11])[N:4]=1)[NH:1][C:12]1[NH:13][C:14]([C:19]#[N:20])=[C:15]([C:17]#[N:18])[N:16]=1

Participants

5

Reactant 2

HCID 1049PyridineHCID 136388401HCID 136388401, compound

Product 1

HCID 20358860HCID 20358860, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

2.65 g of 2,2'-azobis(4,5-imidazoledicarbonitrile) was placed in a flask with 65 ml of pyridine and 25 ml of galcial acetic acid. The slurry was then purged and deoxygenated thoroughly with a stream of nitrogen. Then 3 equivalents (1.95 g) of zinc dust was added. An immediate green/black solution was formed characteristic of a radical anion species. This slowly faded to a pale green as the last of the intermediate reacted. The mixture was filtered under nitrogen to remove excess zinc salts. This gave a pale yellow solution of 2,2'-hydrazobis(4,5-imidazoledicarbonitrile). Exposure of an aliquot to the air caused immediate air oxidation back to the bright yellow azo compound which precipitated as the bis pyridinium salt.

Workup

  1. customThe slurry was then purged
  2. customdeoxygenated thoroughly with a stream of nitrogen
  3. customAn immediate green/black solution was formed characteristic of a radical anion species
  4. customreacted
  5. filtrationThe mixture was filtered under nitrogen
  6. customto remove excess zinc salts

Sources & evidence

ORD record
ord-779c632f39cd4b028b4369303e49c2e0
Source dataset
uspto-grants-1978_04
Patent number
US04083843

Reaction notes

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