Pyrazinecarbonitrile → 2-(5-pyrazin-2-yl-4H-1,2,4-triazol-3-yl)pyrazine

HRID 263123

Reaction equation

HRID 263123 reaction equation
[Na].[C:2]([C:4]1[CH:9]=[N:8][CH:7]=[CH:6][N:5]=1)#[N:3].[N:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:16]([NH:18][NH2:19])=O>CO>[N:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:16]1[N:3]=[C:2]([C:4]2[CH:9]=[N:8][CH:7]=[CH:6][N:5]=2)[NH:19][N:18]=1

Participants

5

Reactant 3

HCID 73172PyrazinecarbonitrileHCID 258796Pyrazine-2-Carboxylic Acid HydrazideHCID 5360545Sodium

Product 1

HCID 135247872-(5-pyrazin-2-yl-4H-1,2,4-triazol-3-yl)pyrazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium (50 mg.) is added to 2-cyanopyrazine (1 gram, 0.01 mole) in 20 ml. of methanol. The solution is allowed to stand 1 hour at room temperature and is added to a suspension of pyrazine carboxylic acid hydrazide (1.4 grams, 0.01 mole) in 50 ml. of methanol. The reaction mixture is heated at reflux for 2 hours and then at room temperature for 16 hours. After cooling, the intermediate acylamidrazone is removed by filtration and is then heated at temperatures between 200° to 260° C. over two and one-half hours. After cooling and recrystallization from methanol-water, 0.8 grams of 3,5-dipyrazinyl-1,2,4-triazole, m.p. 269°-270.5° C. is obtained.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 2 hours
  3. waitat room temperature for 16 hours
  4. temperatureAfter cooling
  5. customthe intermediate acylamidrazone is removed by filtration
  6. temperatureis then heated at temperatures between 200° to 260° C. over two and one-half hours
  7. temperatureAfter cooling
  8. customrecrystallization from methanol-water, 0.8 grams of 3,5-dipyrazinyl-1,2,4-triazole
  9. customm.p. 269°-270.5° C. is obtained

Sources & evidence

ORD record
ord-f65b659f63b7424885cd67184be15dd7
Source dataset
uspto-grants-1979_05
Patent number
US04156085

Linked notes

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