Ethanol → HCID 117899715, compound

HRID 522440Notes

Reaction equation

HRID 522440 reaction equation
C(O)C.Cl[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([S:18][CH2:19][C:20]([F:23])([F:22])[F:21])[CH:12]=1.[S-:24][C:25]#[N:26].[K+].[I-].[K+]>C(OCC)(=O)C.CCCCCC>[S:24]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([S:18][CH2:19][C:20]([F:23])([F:22])[F:21])[CH:12]=1)[C:25]#[N:26]

Participants

7

Reactant 4

HCID 702EthanolHCID 4875Potassium IodideHCID 516872Potassium thiocyanateHCID 117899761HCID 117899761, compound

Product 1

HCID 117899715HCID 117899715, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 100 ml of ethanol were added 2.0 g (6.1 mmol) of 5-chloropentyl-{4-methyl-3-(2,2,2-trifluoroethylthio)phenyl}ether, 4.0 g (41 mmol) of potassium thiocyanate and 0.10 g (0.61 mmol) of potassium iodide. The mixture was refluxed for 10 hours under heating and then allowed to cool to room temperature. The solvent was distilled off under reduced pressure. To the residue was added ethyl acetate to conduct extraction. The organic phase obtained was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=10:1), to obtain 1.8 g (yield: 84%) of an intended product.

Workup

  1. temperatureThe mixture was refluxed for 10 hours
  2. temperatureunder heating
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionTo the residue was added ethyl acetate
  5. extractionextraction
  6. customThe organic phase obtained
  7. washwas washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-961926e4bcea4df7baf8cda7de663e4a
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

Loading…