Lawesson's reagent → HCID 14510227, compound

HRID 1709752Notes

Reaction equation

HRID 1709752 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[F:23][C:24]1[CH:25]=[C:26]([N:30]([CH3:39])[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=O)[CH:27]=[CH:28][CH:29]=1>C1(C)C=CC=CC=1>[F:23][C:24]1[CH:25]=[C:26]([N:30]([CH3:39])[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[S:10])[CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 23036709HCID 23036709, compound

Product 1

HCID 14510227HCID 14510227, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Lawesson's reagent (3.20 g, 7.9 mmol) and N-(3-fluorophenyl)-N-methyl-2-pyridinecarboxamide (3.51 g, 15.2 mmol) were heated to reflux in toluene (45 mL) under nitrogen for 2 hours. The residue, after evaporation of the solvent, was dissolved in dichloromethane, preadsorbed onto silica gel, and flash chromatographed (250 g of silica gel eluted with 10% ethyl acetate in petroleum ether) to yield N-(3-fluorophenyl)-N-methyl-2-pyridinecarbothioamide, as a yellow solid (1.70 g, 45%), m.p. 100°-103° C.

Workup

  1. customThe residue, after evaporation of the solvent
  2. dissolutionwas dissolved in dichloromethane
  3. customchromatographed
  4. wash(250 g of silica gel eluted with 10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-35e7bc1bb30045cea34fcd37706a4050
Source dataset
uspto-grants-1990_08
Patent number
US04950762

Reaction notes

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