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

HRID 401508Notes

Reaction equation

HRID 401508 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-b4e2dcc0e8c540aa99262f8e64454dec
Source dataset
uspto-grants-2014_06
Patent number
US08741936B2

Reaction notes

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