Phenylacetyl chloride → Phenylacetyl isothiocyanate

HRID 1881757Notes

Reaction equation

HRID 1881757 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Pb](SC#N)[S:12][C:13]#[N:14]>C1(C)C=CC=CC=1>[C:1]1([CH2:7][C:8]([N:14]=[C:13]=[S:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7679Phenylacetyl chlorideHCID 516874Bleirhodanid

Product 1

HCID 12454157Phenylacetyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

To a 250 mL round bottom flask was added phenylacetylchloride (15.0 g, 97.0 mmol) and toluene (70 mL) followed by lead (II) thiocyanate (25.7 g, 97.0 mmol). Upon completion of addition, the resulting suspension was stirred at 85° C. for 18 h. After this time, the resulting solids were separated by vacuum filtration, and the filtrate was concentrated by rotary evaporation to provide a residue. The residue was purified via silica gel chromatography (10% EtOAc:Hex) to yield the title compound as a pale yellow, non-viscous oil (12.2 g, 68.8 mmol, 71%). 1H NMR (400 MHz, CDCl3): δ ppm 7.41-7.30 (m, 3H), 7.29-7.23 (m, 2H), 3.85 (s, 2H).

Workup

  1. additionUpon completion of addition
  2. customAfter this time, the resulting solids were separated by vacuum filtration
  3. concentrationthe filtrate was concentrated by rotary evaporation
  4. customto provide a residue
  5. customThe residue was purified via silica gel chromatography (10% EtOAc:Hex)

Sources & evidence

ORD record
ord-4d4ab598cb1743beb9261e340fc2fb4e
Source dataset
uspto-grants-2012_11
Patent number
US08318941B2

Reaction notes

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