Potassium Cyanide → HCID 70817665, compound

HRID 82227Notes

Reaction equation

HRID 82227 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[N:5][N:6]([CH:12]([CH3:14])[CH3:13])[C:7]=1[C:8]([F:11])([F:10])[F:9].[C-:15]#[N:16].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1.O.CCOC(C)=O>[CH:12]([N:6]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:3]([CH2:2][C:15]#[N:16])[CH:4]=[N:5]1)([CH3:14])[CH3:13]

Participants

7

Reactant 2

HCID 9032Potassium CyanideHCID 664366344-(chloromethyl)-1-isopropyl-5-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 70817665HCID 70817665, compoundYield 100%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Tetrabutyl ammonium bromide (7.95 gm, 24.7 mmol) was added to 4-(chloromethyl)-1-isopropyl-5-(trifluoromethyl)-1H-pyrazole (7 g, 31 mmol) in dioxane (75 mL) and water (75 mL) and the mixture was stirred for 10 min. Potassium cyanide (7.42 g, 114 mmol) was added and the mixture was stirred for 16 hours at room temperature. The mixture was diluted with EtOAc (100 mL) then the organic phase was washed with water (100 mL), brine (100 mL) and dried over sodium sulphate. The filtrate was evaporated in vacuo and purified by column chromatography on silica gel (hexane:EtOAc 90:10) to afford the title compound as a white solid in 100% yield, 7.00 g.

Workup

  1. stirringthe mixture was stirred for 16 hours at room temperature
  2. washthe organic phase was washed with water (100 mL), brine (100 mL)
  3. dry with materialdried over sodium sulphate
  4. customThe filtrate was evaporated in vacuo
  5. custompurified by column chromatography on silica gel (hexane:EtOAc 90:10)

Sources & evidence

ORD record
ord-2cc2460879b54b2b848eb5727a989389
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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