Potassium Cyanide → HCID 19349422, compound

HRID 2107780Notes

Reaction equation

HRID 2107780 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)=[CH:4][C:3]=1[C:14]([CH3:18])([CH3:17])[C:15]#[N:16].[C-:19]#[N:20].[K+]>CN(C)C=O>[C:19]([C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)=[CH:4][C:3]=1[C:14]([CH3:18])([CH3:17])[C:15]#[N:16])#[N:20]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 19349440HCID 19349440, compound

Product 1

HCID 19349422HCID 19349422, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[2-bromo-5-(1H-1,2,4-triazol-1-ylmethyl)-phenyl]-2-methylpropiononitrile (0.15 g), dimethylformamide (2 ml) and cuprous cyanide (0.09 g) was stirred and heated under reflux for 8 h. The cooled mixture was treated with aqueous potassium cyanide solution (10 ml) and the mixture was stirred for 10 minutes, then extracted three times with dichloromethane. The combined extracts were dried and evaporated to dryness under reduced pressure, and the residue was purified by flash chromatography, using methanol (2% by volume) in chloroform as eluant, to give 2-[2-cyano-5-(1H-1,2,4-triazol-yl methyl)phenyl]-2-methylpropiononitrile, characterised as the hydrochloride salt mp 159°-166°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 8 h
  3. stirringthe mixture was stirred for 10 minutes
  4. extractionextracted three times with dichloromethane
  5. customThe combined extracts were dried
  6. customevaporated to dryness under reduced pressure
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-dd81057640b242c0a51df30083a4c154
Source dataset
uspto-grants-1990_06
Patent number
US04935437

Reaction notes

Loading…