Echinopsine → 1-Methylquinoline-4(1H)-thione

HRID 1165287Notes

Reaction equation

HRID 1165287 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=O)[CH:4]=[CH:3]1.COC1C=CC(P2(=S)SP(C3C=CC(OC)=CC=3)(=S)[S:22]2)=CC=1>C1C=CC=CC=1>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[S:22])[CH:4]=[CH:3]1

Participants

4

Reactant 2

HCID 6748EchinopsineHCID 87949Lawesson's reagent

Product 1

HCID 2204641-Methylquinoline-4(1H)-thioneYield 165.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Under an inert atmosphere, 1 g of 1-methyl-4-quinolone was dissolved in 20 ml of benzene and then under bigorous stirring, 1.27 g of 2,4-bis-(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane (Lawesson's reagent) was added all at once with stirring for 1 hour at reflux. After cooling and concentrating to dryness by distilling under reduced pressure, the 2.5 g of residue were chromatographed on silica and eluted with a mixture of methyl chloride and methanol (9/1) to obtain 910 mg of the expected product melting at 208°-210° C.

Workup

  1. temperatureat reflux
  2. temperatureAfter cooling
  3. concentrationconcentrating to dryness
  4. distillationby distilling under reduced pressure
  5. customthe 2.5 g of residue were chromatographed on silica
  6. washeluted with a mixture of methyl chloride and methanol (9/1)

Sources & evidence

ORD record
ord-17acc7994a86471ba82bf02242f7f980
Source dataset
uspto-grants-1990_03
Patent number
US04908359

Reaction notes

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