Lawesson's reagent → HCID 86721235, compound

HRID 1750391Notes

Reaction equation

HRID 1750391 reaction equation
[F:1][CH:2]([F:18])[N:3]1[CH:7]=[C:6]([C:8]([NH2:10])=O)[C:5]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[N:4]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>C1COCC1>[F:1][CH:2]([F:18])[N:3]1[CH:7]=[C:6]([C:8](=[S:28])[NH2:10])[C:5]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[N:4]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86721236HCID 86721236, compound

Product 1

HCID 86721235HCID 86721235, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the mixture (1.15 g, 4.51 mmol) obtained in step 3 in THF (18.8 mL) was added Lawesson's reagent (1.46 g, 3.61 mmol) at room temperature, and the mixture was stirred at 60° C. for 3 hr. After cooling to room temperature, and the reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent; 7% ethyl acetate/hexane) to give a mixture (0.840 g, 68%, 1:1.92 mol/mol) of 1-(difluoromethyl)-3-(4-fluorophenyl)-1H-pyrazole-4-carbothioamide and 1-(difluoromethyl)-5-(4-fluorophenyl)-1H-pyrazole-4-carbothioamide as a pale-green powder.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (solvent; 7% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c11c396b78cd4439a93bf98e2fe1006e
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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