Acetonitrile → Phenylacetyl isothiocyanate

HRID 492833Notes

Reaction equation

HRID 492833 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S-:11][C:12]#[N:13].[K+].C(#N)C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:1]1([CH2:7][C:8]([N:13]=[C:12]=[S:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7679Phenylacetyl chlorideHCID 516872Potassium thiocyanateHCID 516892Sodium Bicarbonate

Product 1

HCID 12454157Phenylacetyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To 2-phenylacetyl chloride (36.6 mg) was added potassium thiocyanate (53.8 mg) and acetonitrile (3 ml) under a nitrogen atmosphere, followed by stirring at 60° C. for 2 hrs. The reaction mixture was cooled down to room temperature, and then ethyl acetate (20 ml) and a saturated aqueous solution of sodium hydrogencarbonate (20 ml) were added thereto, followed by stirring for 30 min. After partitioning the solution, the separated organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (20 ml), water (20 ml) and brine (20 ml) in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated to provide phenylacetyl isothiocyanate as a yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringby stirring for 30 min
  3. customAfter partitioning the solution
  4. washthe separated organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (20 ml), water (20 ml) and brine (20 ml) in this order
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-59225088d9d0469892522f28f6392a43
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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