Potassium Cyanide → HCID 19349422, compound

HRID 1636818Notes

Reaction equation

HRID 1636818 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-23ce15e422e64bc3915c0e040244e7fa
Source dataset
uspto-grants-2000_03
Patent number
USRE036617

Reaction notes

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