Lawesson's reagent → HCID 86702823, compound

HRID 1850064Notes

Reaction equation

HRID 1850064 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]1(/[CH:29]=[CH:30]/[CH2:31][C:32]([NH2:34])=O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[C:23]1(/[CH:29]=[CH:30]/[CH2:31][C:32](=[S:10])[NH2:34])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 14386648HCID 14386648, compound

Product 1

HCID 86702823HCID 86702823, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Lawesson's reagent (1.88 g, 4.65 mmol) was added to (E)-4-phenylbut-3-enamide (500 mg, 3.10 mmol) in toluene (25 mL). The reaction mixture was refluxed for 24 h then cooled to room temperature. The solvent was then removed under reduced pressure. The crude residue was purified twice by column chromatography to give >90% pure (E)-4-phenylbut-3-enethioamide (320 mg).

Workup

  1. temperatureThe reaction mixture was refluxed for 24 h
  2. customThe solvent was then removed under reduced pressure
  3. customThe crude residue was purified twice by column chromatography

Sources & evidence

ORD record
ord-4c2570d8165f498c892722674369923a
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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