Lawesson's reagent → HCID 13654176, compound

HRID 280461Notes

Reaction equation

HRID 280461 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]([C:25]1[N:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:28]=[CH:27][C:26]=1[C:36]([NH:38][CH3:39])=O)#[N:24]>C1(C)C=CC=CC=1>[C:23]([C:25]1[N:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:28]=[CH:27][C:26]=1[C:36](=[S:10])[NH:38][CH3:39])#[N:24]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 1636751H-Pyrazole-4-carboxamide, 5-cyano-N-methyl-1-phenyl-

Product 1

HCID 13654176HCID 13654176, compoundYield 7.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Eight grams of Lawesson's Reagent was added to a stirring solution of 3 g of 5-cyano-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide in 75 ml of toluene. The reaction mixture was refluxed for approximately 1 hour and the solution was evaporated to dryness. The residue was dissolved in methylene chloride and filtered. The filtrate was concentrated under reduced pressure and the residue was chromatographed employing high pressure liquid chromatography and methylene chloride as the eluent. Fractions containing the second spot were combined and the solvent was evaporated therefrom. The residue was recrystallized from toluene to provide 250 mg of 5-cyano-N-methyl-1-phenyl-1H-pyrazole-4-thiocarboxamide, MP=215°-217° C.

Workup

  1. temperatureThe reaction mixture was refluxed for approximately 1 hour
  2. customthe solution was evaporated to dryness
  3. dissolutionThe residue was dissolved in methylene chloride
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was chromatographed
  7. additionFractions containing the second spot
  8. customthe solvent was evaporated
  9. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-325d5d2055b04479b74ec9b17cd67fde
Source dataset
uspto-grants-1986_05
Patent number
US04589905

Reaction notes

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