Sodium Cyanide → 5-Methyl-2-phenyl-2H-1,2,3-triazole-4-acetonitrile

HRID 478335Notes

Reaction equation

HRID 478335 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH2:5][C:6]1[C:10]([CH3:11])=[N:9][N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]=1.[OH-].[Na+]>CN(C=O)C>[CH3:11][C:10]1[C:6]([CH2:5][C:1]#[N:2])=[N:7][N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:9]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 14798Sodium HydroxideHCID 338434HCID 338434, compound

Product 1

HCID 5632655-Methyl-2-phenyl-2H-1,2,3-triazole-4-acetonitrileYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.8 g of sodium cyanide was suspended in 30 ml of DMF, and 5.0 g of 4-chloromethyl-5-methyl-2-phenyl-1,2,3-triazol was added under cooling with ice. After stirring for 3 hours at room temperature, an aqueous solution of sodium hydroxide was added to the reaction solution to make it alkaline, and extracted with toluene. The organic phase was washed with water and a saturated salt solution, then dried over anhydrous sodium sulfate. After the solvent was distilled off, the deposited crystals were washed with hexane to obtain 4.3 g of the aimed compound.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with toluene
  3. washThe organic phase was washed with water
  4. dry with materiala saturated salt solution, then dried over anhydrous sodium sulfate
  5. distillationAfter the solvent was distilled off
  6. washthe deposited crystals were washed with hexane

Sources & evidence

ORD record
ord-7991a7dcb39a4bcfb2dd08149983ef8e
Source dataset
uspto-grants-2003_11
Patent number
US06642234B1

Reaction notes

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