Lawesson's reagent → HCID 86002050, compound

HRID 1986049Notes

Reaction equation

HRID 1986049 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][C:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[CH:8][C:7]2=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>C1(C)C=CC=CC=1>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[O:10][C:11]3[C:6]([C:7](=[S:30])[CH:8]=2)=[CH:5][CH:4]=[CH:3][C:2]=3[CH3:1])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 6886834'-Methoxy-8-methylflavone

Product 1

HCID 86002050HCID 86002050, compoundYield 125.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound I-23 was prepared according to the general method described above in Scheme 1. A stirred mixture of 8-methyl-4′-methoxyflavone (200.0 mg, 0.75 mmol), Lawesson's reagent (182.3 mg, 0.45 mmol) and anhydrous toluene (4.0 mL) was refluxed under N2 for 1.5 hr. The solvent was removed under vacuum and the residue was purified by silica gel chromatography (20% ethyl acetate/hexane) to give 2-(4-Methoxy-phenyl)-8-methyl-chromene-4-thione (160.0 mg, 75.5% yield) as a red solid. Thione was used in next step without further purification. LC/MS: (M+H) 283.1. LC/Method A/8.967 min, 90.0% purity by area %.

Workup

  1. customCompound I-23 was prepared
  2. temperaturewas refluxed under N2 for 1.5 hr
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by silica gel chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1c23b695185c4b8ebfc679dc150c25eb
Source dataset
uspto-grants-2009_06
Patent number
US07547794B2

Reaction notes

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