Lawesson's reagent → HCID 86721245, compound

HRID 1750402Notes

Reaction equation

HRID 1750402 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:8]([C:18]([NH2:20])=O)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>C1COCC1>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:8]([C:18](=[S:30])[NH2:20])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86721246HCID 86721246, compound

Product 1

HCID 86721245HCID 86721245, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound (1.45 g, 5.30 mmol) obtained in step 10 and Lawesson's reagent (2.146 g, 5.30 mmol) in THF (25 mL) was stirred at 60° C. for 20 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by NH-silica gel column chromatography (solvent gradient; 2→60% ethyl acetate/hexane) to give 1-tert-butyl-5-(4-methoxyphenyl)-1H-pyrazole-4-carbothioamide (0.81 g, 2.80 mmol, 53%) 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→60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9553094fe0ad4a96a466ea56286df1bc
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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