Methyl iodide → 3,5-diamino-1-methyl-1H-pyrazole-4-carbonitrile

HRID 261072Notes

Reaction equation

HRID 261072 reaction equation
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([NH2:9])[NH:4][N:3]=1.IC.[C:12](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([NH2:9])[N:4]([CH3:12])[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 142021413,5-Diamino-1H-pyrazole-4-carbonitrile

Product 1

HCID 126210283,5-diamino-1-methyl-1H-pyrazole-4-carbonitrileYield 16.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3,5-Diamino-4-cyanopyrazole (6.1 g) prepared as in Example 3, iodomethane (3.1 ml), anhydrous potassium carbonate (7.6 g) and acetone (120 ml) were heated under reflux for 18 hours. The mixture was filtered, and the filtrate was concentrated to a viscous oil. Trituration of the oil with water gave a precipitate of 3,5-diamino-4-cyano-1-methylpyrazole (1.1 g), m.p. 194°-196° C.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 18 hours
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated to a viscous oil

Sources & evidence

ORD record
ord-027954cc5b4a46fdabac1c15a9c3705b
Source dataset
uspto-grants-1979_08
Patent number
US04163846

Reaction notes

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