Phenylacetonitrile → 2-Phenylethanethioamide

HRID 1067416Notes

Reaction equation

HRID 1067416 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])(OCC)(SCC)=[S:11]>Cl.C(OCC)(=O)C>[C:1]1([CH2:7][C:8]([NH2:9])=[S:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8794PhenylacetonitrileHCID 53249491Diethyldithiophosphate

Product 1

HCID 7313682-PhenylethanethioamideYield 55%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

A solution of phenylacetonitrile (10.0 g, 85.4 mmol) and diethyl dithiophosphate (17.5 g, 93.9 mmol) in 4N-HCl/ethyl acetate (400 mL) was stirred at room temperature for 16 hours. This reaction mixture was washed with water and saturated aqueous sodium hydrogen carbonate solution, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from ethanol to provide 7.1 g of the title compound. Yield 55%.

Workup

  1. washThis reaction mixture was washed with water and saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-b95e9b3ac9114e76baa3b07b56de8fcd
Source dataset
uspto-grants-2001_06
Patent number
US06248766B1

Reaction notes

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