Sodium Cyanide → HCID 58542582, compound

HRID 1843068Notes

Reaction equation

HRID 1843068 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12](F)=[C:11]([C:14]([F:17])([F:16])[F:15])[C:10]([C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C-:25]#[N:26].[Na+].O.C(OCC)C>C(#N)C>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:25]#[N:26])=[C:11]([C:14]([F:15])([F:17])[F:16])[C:10]([C:18]([F:23])([F:24])[C:19]([F:20])([F:21])[F:22])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 21584184Diethylether waterHCID 58542581HCID 58542581, compound

Product 1

HCID 58542582HCID 58542582, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.95 g (5.1 mmol) of 3-chloro-2-[5-fluor-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-1-yl]pyridine and 0.30 g (6.1 mmol) of sodium cyanide are suspended in 20 ml of acetonitrile and the reaction mixture is then stirred under reflux for 16 hours. After cooling, the reaction mixture is poured onto a water/diethyl ether mixture. The aqueous phase is extracted three times with diethyl ether. The combined organic phases are washed twice with water and once with saturated sodium chloride solution and then dried over magnesium sulphate and filtered. The solvent is removed under reduced pressure on a rotary evaporator. The crude product is purified by means of flash chromatography on silica gel. This gives 1.7 g of 3-chloro-2-[5-cyano-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-1-yl]pyridine (84%) as a yellow oil.

Workup

  1. temperatureunder reflux for 16 hours
  2. temperatureAfter cooling
  3. extractionThe aqueous phase is extracted three times with diethyl ether
  4. washThe combined organic phases are washed twice with water and once with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customThe solvent is removed under reduced pressure on a rotary evaporator
  8. customThe crude product is purified by means of flash chromatography on silica gel

Sources & evidence

ORD record
ord-ad60548ea08b40ea9bcb3e4a686c3768
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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