Potassium Cyanide → HCID 86617535, compound

HRID 2238533Notes

Reaction equation

HRID 2238533 reaction equation
F[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].[C-:21]#[N:22].[K+]>CS(C)=O>[C:21]([C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])#[N:22]

Participants

4

Reactant 2

HCID 9032Potassium Cyanide2×HCID 86617534HCID 86617534, compound

Product 1

HCID 86617535HCID 86617535, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

1,1-Dimethylethyl {[2-fluoro-3-(trifluoromethyl)phenyl]methyl}carbamate (1.17 g, 4 mmol) was dissolved in dimethylsulphoxide (5 ml) and treated with potassium cyanide (0.260 g, 4 mmol). The mixture was then heated at 80° C. under argon for 1.5 hrs and then at 120° C. overnight (16 hrs). Additional potassium cyanide (0.260 g, 4 mmol) was then added and heating continued at 120° C. for a further 24 hrs. The mixture was then cooled to room temperature, quenched with water, and diluted with ethyl acetate. The organic extracts were separated and washed three times with water and then with saturated aqueous sodium chloride solution. Drying and evaporation gave a brown gum which was purified by silica-gel column chromatography, eluting with a 1:10-1:5 gradient of ethyl acetate in hexanes, to give partially pure 1,1-dimethylethyl {[2-cyano-3-(trifluoromethyl)phenyl]methyl}carbamate as a dark solid/semi-solid which was used in the next step without further purification.

Workup

  1. customat 120° C.
  2. customovernight (16 hrs)
  3. temperatureheating
  4. temperatureThe mixture was then cooled to room temperature
  5. customquenched with water
  6. additiondiluted with ethyl acetate
  7. customThe organic extracts were separated
  8. washwashed three times with water
  9. customDrying
  10. customevaporation
  11. customgave a brown gum which
  12. customwas purified by silica-gel column chromatography
  13. washeluting with a 1:10-1:5 gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-38fc121e96074ffba0809a0ccaafeea2
Source dataset
uspto-grants-2010_05
Patent number
US07718693B2

Reaction notes

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