Ethanol → HCID 117899724, compound

HRID 522456Notes

Reaction equation

HRID 522456 reaction equation
C(O)C.Br[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([S:18][CH2:19][C:20]([F:23])([F:22])[F:21])[C:15]([CH3:24])=[CH:14][C:13]=1[CH3:25].[S-:26][C:27]#[N:28].[K+].CCCCCC>C(OCC)(=O)C>[S:26]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([S:18][CH2:19][C:20]([F:23])([F:22])[F:21])[C:15]([CH3:24])=[CH:14][C:13]=1[CH3:25])[C:27]#[N:28]

Participants

6

Reactant 4

HCID 702EthanolHCID 8058HexaneHCID 516872Potassium thiocyanateHCID 117899784HCID 117899784, compound

Product 1

HCID 117899724HCID 117899724, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 60 ml of ethanol were added 1.87 g (4.68 mmol) of 6-bromohexyl-[2,4-dimethyl-5-(2,2,2-trifluoroethylthio)phenyl]ether and 2.28 g (23.46 mmol) of potassium thiocyanate. The mixture was refluxed for 8 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 ethyl acetate and water. 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=20:1), to obtain 1.37 g (yield: 77%) of an intended product.

Workup

  1. temperatureThe mixture was refluxed for 8 hours
  2. temperatureunder heating
  3. distillationthe solvent was distilled off under reduced pressure
  4. extractionThen extraction
  5. additionby adding ethyl acetate and water
  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-7bc33055bacf44f6b506cbcb0bcdc79d
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

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