HCID 18929395, compound → HCID 18929420, compound

HRID 1598519Notes

Reaction equation

HRID 1598519 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13]1[C:17]([N+:18]([O-])=O)=[C:16]([S:21][CH3:22])[N:15]([CH3:23])[N:14]=1.[H][H]>C(O)C.[C].[Pd]>[NH2:18][C:17]1[C:13]([C:3]2[C:4]([Cl:12])=[CH:5][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:7][C:2]=2[Cl:1])=[N:14][N:15]([CH3:23])[C:16]=1[S:21][CH3:22]

Participants

5

Reactant 2

HCID 18929395HCID 18929395, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 18929420HCID 18929420, compoundYield 433.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A suspension of 0.15 g of 3-(2,6-dichloro-4-trifluoromethylphenyl)-1-methyl-5-methylsulfenyl-4-nitropyrazole (compound 13) and 0.1 g of 10% palladium carbon in ethanol was stirred for 1 hour while introducing hydrogen gas into the mixture at room temperature at atmospheric pressure. The reaction mixture was filtered through Celite, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography on silica gel (eluent: ether/hexane=1/4) to obtain 0.6 g of the desired compound in the form of a consistent liquid (yield 67.3%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe resulting residue was purified by column chromatography on silica gel (eluent: ether/hexane=1/4)

Sources & evidence

ORD record
ord-5d2de8b9b0974edaa6cac8977b82b501
Source dataset
uspto-grants-1998_04
Patent number
US05739083

Reaction notes

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