Lawesson's reagent → 1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazole-4-carbothioamide

HRID 1750342Notes

Reaction equation

HRID 1750342 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17]([NH2:19])=O)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>C1COCC1>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17](=[S:29])[NH2:19])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 867211791-tert-butyl-5-(4-fluorophenyl)-1H-pyrazole-4-carboxamide

Product 1

HCID 867211801-tert-butyl-5-(4-fluorophenyl)-1H-pyrazole-4-carbothioamideYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound (4.00 g, 15.31 mmol) obtained in step 3 and Lawesson's reagent (6.19 g, 15.31 mmol) in THF (50 mL) was stirred at 50° C. for 1.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by NH-silica gel column chromatography (solvent gradient; 2→65% ethyl acetate/hexane) to give 1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazole-4-carbothioamide (2.75 g, 9.91 mmol, 65%) as a pale-yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by NH-silica gel column chromatography (solvent gradient; 2→65% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-39e1fccf05b149bf8d12a9fcce7ee535
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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