Lawesson's reagent → 2-Methylfuran-3-carbothioamide
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
Product 1
Reagents, catalysts & solvents 1
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
- temperaturewas refluxed for 3 hours
- temperatureThe reaction mixture was then cooled
- filtrationfiltered through a plug of neutral aluminum oxide
- washeluted with ether
- 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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