Lawesson's reagent → HCID 86721260, compound

HRID 1750415Notes

Reaction equation

HRID 1750415 reaction equation
[CH:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[C:10]([C:19]([NH2:21])=O)[CH:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>C1COCC1>[CH:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[C:10]([C:19](=[S:31])[NH2:21])[CH:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86721258HCID 86721258, compound

Product 1

HCID 86721260HCID 86721260, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound (284 mg, 0.99 mmol) obtained in step 1 and Lawesson's reagent (360 mg, 0.89 mmol) in THF (4 mL) was stirred at 60° C. for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by NH-silica gel column chromatography (solvent gradient; 5→95% ethyl acetate/hexane) to give 1-cyclohexyl-5-(4-fluorophenyl)-1H-pyrazole-4-carbothioamide (236 mg, 0.778 mmol, 79%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by NH-silica gel column chromatography (solvent gradient; 5→95% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5ec42287ceba4a81a6d91ff48e07c344
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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