Lawesson's reagent → HCID 86750966, compound

HRID 1683812Notes

Reaction equation

HRID 1683812 reaction equation
[C:1]1([N:7]2[C:11](=O)[CH2:10][C:9]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>C1(C)C=CC=CC=1>[C:1]1([N:7]2[C:11](=[S:29])[CH2:10][C:9]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 12632313HCID 12632313, compound

Product 1

HCID 86750966HCID 86750966, compoundYield 147.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5.6 g (20 mmol) of 1-phenyl-3-(4-methylphenyl)-4, 5-dihydropyrazol-5-one, 6.1 g (15 mmol) of Lawesson's reagent and 50 ml of toluene was heated under reflux for 2 hours. The reaction solution was concentrated, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1 (v/v)) and recrystallized from diethyl ether-n-hexane to give quantitatively 5.9 g of the object compound as pale yellow crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction solution was concentrated
  4. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1 (v/v))
  5. customrecrystallized from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-f71fbb4c13c6413fb522099f28b11843
Source dataset
uspto-grants-1997_06
Patent number
US05639776

Reaction notes

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