Lawesson's reagent → 2(1H)-Pyridinethione, 1-ethyl-

HRID 1165288Notes

Reaction equation

HRID 1165288 reaction equation
[CH2:1]([N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=O)[CH3:2].COC1C=CC(P2(=S)SP(C3C=CC(OC)=CC=3)(=S)[S:19]2)=CC=1>C1C=CC=CC=1>[CH2:1]([N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=[S:19])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 1394342(1H)-Pyridinone, 1-ethyl-

Product 1

HCID 5491942(1H)-Pyridinethione, 1-ethyl-Yield 187%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Under an inert atmosphere, 1.23 g of 1-ethyl-2-pyridone and 25 ml of benzene were mixed together and then under vigorous stirring, 2.02 g of 2,4-bis-(4-methoxyphenyl)-2,4-dithioxo1,3,2,4-dithiadiphosphetane (Lawesson's reagent) were added all at once with stirring at reflux for 2 hours. After cooling and filtering, the filtrate was taken to dryness by distilling under reduced pressure, and the 3.8 g of residue were chromatographed on silica and eluted with a mixture of methylene chloride and ethyl acetate (8/2) to obtain 1.3 g of the expected product melting at about 50° C.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureAfter cooling
  3. filtrationfiltering
  4. distillationby distilling under reduced pressure
  5. customthe 3.8 g of residue were chromatographed on silica
  6. washeluted with a mixture of methylene chloride and ethyl acetate (8/2)

Sources & evidence

ORD record
ord-31d373a235a9447ca23d35635c6b7e64
Source dataset
uspto-grants-1990_03
Patent number
US04908359

Reaction notes

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