Lawesson's reagent → HCID 13822014, compound

HRID 1731263Notes

Reaction equation

HRID 1731263 reaction equation
[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14]([NH:16][CH3:17])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:27])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[S:27])[NH:16][CH3:17]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 1757891H-Pyrazole-4-carboxamide, 5-chloro-1-(3-chlorophenyl)-N-methyl-

Product 1

HCID 13822014HCID 13822014, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3.0 g of 5-chloro-1-(3-chlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide and 6.5 g of Lawesson's Reagent in 150 ml toluene was refluxed for one hour. The solution was cooled and the volatiles were removed under reduced pressure. The residue was chromatographed over silica gel eluting with methylene chloride. The fractions containing the major component were combined and the solvent was evaporated therefrom to afford 1.6 g, following recrystallization from toluene, of 5-chloro-1-(3-chlorophenyl)-N-methyl-1H-pyrazole-4-thiocarboxamide. Yield 56%. mp=128°-130° C.

Workup

  1. temperatureThe solution was cooled
  2. customthe volatiles were removed under reduced pressure
  3. customThe residue was chromatographed over silica gel eluting with methylene chloride
  4. additionThe fractions containing the major component
  5. customthe solvent was evaporated
  6. customto afford 1.6 g
  7. customrecrystallization from toluene

Sources & evidence

ORD record
ord-5ddbd92fd55c46fda452faf3bee0e706
Source dataset
uspto-grants-1986_11
Patent number
US04620865

Reaction notes

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