Ethanol → 5,6-Dipyridinyl 2,3-pyrazinedicarbonitrile

HRID 635532Notes

Reaction equation

HRID 635532 reaction equation
[CH:1]1[CH:6]=[C:5]([C:7]([C:9]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=O)[N:4]=[CH:3][CH:2]=1.[NH2:17]/[C:18](/[C:23]#[N:24])=[C:19](\[NH2:22])/[C:20]#[N:21].C(O)C.O>C1C=CC=CC=1>[N:4]1[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=1[C:7]1[N:17]=[C:18]([C:23]#[N:24])[C:19]([C:20]#[N:21])=[N:22][C:9]=1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][N:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 68115Di-2-pyridylethanedioneHCID 2723951Diaminomaleonitrile

Product 1

HCID 3963715,6-Dipyridinyl 2,3-pyrazinedicarbonitrileYield 45.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Into a 250 mL round bottomed flask are placed, 2,2′-pyridil (8.48 g, 40 mmol), diaminomaleonitrile (4.32 g, 40 mmol) and 125 mL of ethanol. The flask is fitted with a magnetic stirrer and a condenser, and refluxed for 30 minutes. The mixture is allowed to cool, and 10 mL of water is added. Filtration yielded 8.9 g of crude product as a beige solid. The solid is boiled in benzene (400 mL) and filtered hot. The red filtrate is discarded giving 5.2 g of the title compound as a pale beige solid.

Workup

  1. customInto a 250 mL round bottomed flask are placed
  2. customThe flask is fitted with a magnetic stirrer and a condenser
  3. temperaturerefluxed for 30 minutes
  4. temperatureto cool
  5. filtrationFiltration
  6. customyielded 8.9 g of crude product as a beige solid
  7. filtrationfiltered hot

Sources & evidence

ORD record
ord-0a92cc860ea546ffa68711f55d8c0e1a
Source dataset
uspto-grants-2001_02
Patent number
US06187928B1

Reaction notes

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