Ethanol → HCID 117899767, compound

HRID 522443Notes

Reaction equation

HRID 522443 reaction equation
C(O)C.Br[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([S:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:14]([Cl:23])=[CH:13][C:12]=1[F:24].[S-:25][C:26]#[N:27].[K+].CCCCCC>C(OCC)(=O)C>[S:25]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([S:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:14]([Cl:23])=[CH:13][C:12]=1[F:24])[C:26]#[N:27]

Participants

6

Reactant 4

HCID 702EthanolHCID 8058HexaneHCID 516872Potassium thiocyanateHCID 117899759HCID 117899759, compound

Product 1

HCID 117899767HCID 117899767, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 60 ml of ethanol were added 4.2 g (10.3 mmol) of 5-bromopentyl-[4-chloro-2-fluoro-5-(2,2,2-trifluoroethylthio)phenyl]ether and 5.0 g (51.5 mmol) of potassium thiocyanate. The mixture was refluxed for 4 hours under heating. The mixture was allowed to cool to room temperature, and the solvent was distilled off under reduced pressure. Then extraction was conducted by adding water and ethyl acetate. The organic phase obtained was dried over anhydrous magnesium sulfate and 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 3.9 g (yield: 98%) of an intended product.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. temperatureunder heating
  3. distillationthe solvent was distilled off under reduced pressure
  4. extractionThen extraction
  5. additionby adding water and ethyl acetate
  6. customThe organic phase obtained
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-5385324180ce41f2960b704d098f4ffe
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

Loading…