Pirfenidone → 2(1H)-Pyridinethione, 5-methyl-1-phenyl-

HRID 12424Notes

Reaction equation

HRID 12424 reaction equation
[C:1]1([N:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>C1(C)C=CC=CC=1>[C:1]1([N:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]2=[S:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 40632PirfenidoneHCID 87949Lawesson's reagent

Product 1

HCID 119889472(1H)-Pyridinethione, 5-methyl-1-phenyl-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-phenyl-5-methyl-2-pyridinone (555.7 mg, 3 mmol) was reacted with Lawesson's reagent (606.7 mg, 1.5 mmol) in toluene (5 ml) at 90° C. Reaction mixture was evaporated and the target compound was isolated by column chromatography (20-30% ethyl acetate-hexane) followed by crystallization from methyl-tert-butyl ether. Yield 403 mg (67%), yellow solid. The 1H NMR spectra was consistent with the structure of Compound 18.

Workup

  1. customReaction mixture
  2. customwas evaporated
  3. customthe target compound was isolated by column chromatography (20-30% ethyl acetate-hexane)
  4. customfollowed by crystallization from methyl-tert-butyl ether

Sources & evidence

ORD record
ord-a5e9cfcf879a480fa44c407279407e0b
Source dataset
uspto-grants-2010_06
Patent number
US07728013B2

Reaction notes

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