Lawesson's reagent → HCID 14510215, compound

HRID 1709748Notes

Reaction equation

HRID 1709748 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=O)[CH:5]=[CH:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[S:26])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 4879626HCID 4879626, compound

Product 1

HCID 14510215HCID 14510215, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(3-Fluorophenyl)-2-pyridinecarboxamide (13.0 g, 60 mmol) and Lawesson's reagent (29.2 g, 72 mmol) were refluxed in toluene (180 mL) for 3 hours. The residue obtained after evaporating the solvent was flash chromatographed on silica gel (eluted with 2% ethyl acetate in petroleum ether) and then recrystallized from a mixture of dichloromethane and hexanes to yield a N-(3-fluorophenyl)-2-pyridinecarbothioamide as a yellow solid (6.75 g, 48%) m.p. 72°-76° C.

Workup

  1. customThe residue obtained
  2. customafter evaporating the solvent
  3. customchromatographed on silica gel (eluted with 2% ethyl acetate in petroleum ether)
  4. customrecrystallized from a mixture of dichloromethane and hexanes

Sources & evidence

ORD record
ord-ea0a576e972644dab43c25db275dd75c
Source dataset
uspto-grants-1990_08
Patent number
US04950762

Reaction notes

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