Potassium thiocyanate → HCID 18461195, compound

HRID 2117731Notes

Reaction equation

HRID 2117731 reaction equation
CC1C=CC(S(O[N:12]=[C:13]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)(=O)=O)=CC=1.[Na].[C:29]([S-:31])#[N:30].[K+].C([O-])(O)=O.[Na+]>C(O)C.C(OCC)C>[F:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]2[C:13]([C:22]3[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=3)=[N:12][C:29](=[S:31])[N:30]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 516872Potassium thiocyanateHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 72728375HCID 72728375, compound

Product 1

HCID 18461195HCID 18461195, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Under an atmosphere of argon, 2-(4-fluorophenyl)-1-(4-pyridinyl)ethanone-O-[(4-methylphenyl)sulfonyl]oxime (0.03 mol/10.0 g) was dissolved in 60 ml of absolute ethanol. In an ice bath, the mixture was cooled to 0° C., and a freshly prepared solution of sodium (0.03 M/0.75 g) in 30 ml of absolute ethanol was added dropwise. The reaction mixture was stirred at 0° C. for 1.5 h. After addition of 500 ml of diethyl ether, stirring was continued for 30 min. The resulting precipitate was filtered off and washed 4× with in each case 50 ml of diethyl ether. The combined ether phase was extracted 3× with in each case 90 ml of HCl 10%. The aqueous extract was concentrated to 40 ml, and KSCN (0.05 mol/5.0 g) was added. With stirring, the reaction mixture was then heated under reflux for 1 h. When the mixture was neutralized using 270 ml of 5% strength NaHCO3 solution, the title compound was obtained as a yellow precipitate. The precipitate was filtered off, washed with H2O and dried in a drying cabinet at 60° C. Yield: 5.6 g (79%)

Workup

  1. stirringstirring
  2. waitwas continued for 30 min
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed 4× with in each case 50 ml of diethyl ether
  5. extractionThe combined ether phase was extracted 3× with in each case 90 ml of HCl 10%
  6. extractionThe aqueous extract
  7. additionwas added
  8. stirringWith stirring
  9. temperaturethe reaction mixture was then heated
  10. temperatureunder reflux for 1 h

Sources & evidence

ORD record
ord-24485574cd7245aeadf0a278401803ab
Source dataset
uspto-grants-2008_10
Patent number
US07442713B2

Reaction notes

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