Lawesson's reagent → HCID 18364048, compound
Reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9](=O)[CH2:10][O:11][C:7]=2[CH:6]=[C:5]([O:13][CH3:14])[CH:4]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:8]2[C:9](=[S:24])[CH2:10][O:11][C:7]=2[CH:6]=[C:5]([O:13][CH3:14])[CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
This reaction was performed under nitrogen and anhydrous conditions. 4,6-Dimethoxy-3-benzofuranone (1.5 g, 6.6 mmol) was dissolved in dry toluene (25 ml), and Lawesson's reagent (1.6 g, 4 mmol) was added. The mixture was refluxed with stirring for 18 hours. The mixture was cooled to room temperature and purified by chromatography with 1:1 ether:petroleum ether. Concentration of the fractions yielded yellow/orange crystals. The crystals were washed with the eluent and clean yellow crystals were produced. 1H NMR showed at least two compounds, probably the thioketone and the thiol. Yield: 400 mg (27%). NMR: δ (ppm): 3.86, 3.88, 3.94, 3.96 (OMe, 2 from thioketone and 2 from thiol), δ (ppm): 4.04 (—OCH2C(S)—), δ (ppm): 6.40 6.52 (aromatic).