Dimethyl Sulfate → 3,5-diamino-1-methyl-1H-pyrazole-4-carbonitrile

HRID 261073Notes

Reaction equation

HRID 261073 reaction equation
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([NH2:9])[NH:4][N:3]=1.[CH3:10]OS(OC)(=O)=O>[OH-].[Na+]>[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([NH2:9])[N:4]([CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 142021413,5-Diamino-1H-pyrazole-4-carbonitrile

Product 1

HCID 126210283,5-diamino-1-methyl-1H-pyrazole-4-carbonitrileYield 20.8%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

3,5-Diamino-4-cyanopyrazole (6.1 g) was dissolved in 1 M sodium hydroxide solution (50 ml), and dimethylsulphate (6.2 g) was added. The mixture was heated at reflux for 21/2 hours and then evaporated to dryness. The residue was extracted with 2-methoxyethanol, and the extracts were evaporated. The residue was triturated with a small amount of water to give 3,5-diamino-4-cyano-1-methylpyrazole (1.4 g), m.p. 194°-196° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 21/2 hours
  3. customevaporated to dryness
  4. extractionThe residue was extracted with 2-methoxyethanol
  5. customthe extracts were evaporated
  6. customThe residue was triturated with a small amount of water

Sources & evidence

ORD record
ord-d64a01b7bcd6409887b9085dfe54487f
Source dataset
uspto-grants-1979_08
Patent number
US04163846

Reaction notes

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