Potassium Cyanide → HCID 70817665, compound

HRID 1753096Notes

Reaction equation

HRID 1753096 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 104%

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 minutes. 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 silica gel column chromatography eluting with hexane:EtOAc 90:10 to afford the title compound as a white solid (100%, 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 silica gel column chromatography
  6. washeluting with hexane:EtOAc 90:10

Sources & evidence

ORD record
ord-a6597770d8464096a619b0b7f0e44c97
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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