Lawesson's reagent → HCID 14510218, compound

HRID 1709745Notes

Reaction equation

HRID 1709745 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[NH:31][C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)=O>C1(C)C=CC=CC=1>[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[NH:31][C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)=[S:10]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 2576380HCID 2576380, compound

Product 1

HCID 14510218HCID 14510218, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Lawesson's reagent (29.8 g, 74 mmol) and N-(2,4-difluorophenyl)-2-pyridinecarboxamide (14.37 g, 61 mmol) were combined in toluene (185 mL) and refluxed for 3 hours. After evaporation of the solvent, the residue was dissolved in dichloromethane, preadsorbed on silica gel, and flash chromatographed (eluted with 2% acetate in petroleum ether) to provide N-(2,4-difluorophenyl)-2-pyridinecarbothioamide as a yellow solid (14.45 g, 94%) m.p. 124°-129° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. customAfter evaporation of the solvent
  3. dissolutionthe residue was dissolved in dichloromethane
  4. customchromatographed
  5. wash(eluted with 2% acetate in petroleum ether)

Sources & evidence

ORD record
ord-12abcd4db5634926b86044f9d9cc358e
Source dataset
uspto-grants-1990_08
Patent number
US04950762

Reaction notes

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