Lawesson's reagent → 2-Methylfuran-3-carbothioamide

HRID 1416550Notes

Reaction equation

HRID 1416550 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[C:7]([NH2:9])=O.C(=O)(O)[O-].[Na+].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[C:7](=[S:24])[NH2:9]

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 107729742-Methylfuran-3-carboxamide

Product 1

HCID 126012172-Methylfuran-3-carbothioamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A reaction mixture of N-[4-chloro-3-[dimethylhydrazono)methyl]phenyl]-2-methyl 3-furancarboxamide (1 g), sodium bicarbonate (1.8 g) and Lawesson's reagent (0.9 g) in toluene (20 mL) was refluxed for 3 hours. The reaction mixture was then cooled and filtered through a plug of neutral aluminum oxide and eluted with ether. Evaporation of the solvent produced 0.6 g of N-[4-chloro-3-[dimethylhydrazono)methyl]phenyl]-2-methyl-3-furancarbothioamide, m.p. 90-92° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureThe reaction mixture was then cooled
  3. filtrationfiltered through a plug of neutral aluminum oxide
  4. washeluted with ether
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-cc3e6aa34502418fa51a4f9eb4ec3adf
Source dataset
uspto-grants-1999_06
Patent number
US05914351

Reaction notes

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