Sodium Cyanide → 2-(1-methyl-1H-1,2,4-triazol-5-yl)acetonitrile

HRID 931167Notes

Reaction equation

HRID 931167 reaction equation
Cl.Cl[CH2:3][C:4]1[N:8]([CH3:9])[N:7]=[CH:6][N:5]=1.[C-:10]#[N:11].[Na+]>CS(C)=O>[CH3:9][N:8]1[C:4]([CH2:3][C:10]#[N:11])=[N:5][CH:6]=[N:7]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 222853325-(chloromethyl)-1-methyl-1H-1,2,4-triazole hydrochloride

Product 1

HCID 656015352-(1-methyl-1H-1,2,4-triazol-5-yl)acetonitrileYield 85.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 5-(chloromethyl)-1-methyl-1H-1,2,4-triazole hydrochloride (1.5 g, 11.45 mmol) in dimethylsulfoxide (30 mL) was added to a stirred suspension of sodium cyanide (3.366 g, 68.70 mmol) in dimethylsulfoxide (20 mL), and the reaction mixture was stirred at room temperature for 16 h. The mixture was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and concentrated. The resulting crude product was purified via column chromatography (100-200 mesh silica gel, 10-12% ethyl acetate in petroleum ether) to afford 2-(1-methyl-1H-1,2,4-triazol-5-yl)acetonitrile (1.2 g). MS (ES+APCI) (M+H) 123.2.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe resulting crude product was purified via column chromatography (100-200 mesh silica gel, 10-12% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-ad3ef44cfd8d460eb1984d41c29e21c3
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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