Benzylamine → benzyl(5-bromo-4-nitro-2-propyl-2H-pyrazol-3-yl)amine

HRID 1181154Notes

Reaction equation

HRID 1181154 reaction equation
[CH2:1]([N:4]1[C:8]([Br:9])=[C:7]([N+:10]([O-:12])=[O:11])[C:6]([Br:13])=[N:5]1)[CH2:2][CH3:3].[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CCO>[CH2:14]([NH:21][C:8]1[N:4]([CH2:1][CH2:2][CH3:3])[N:5]=[C:6]([Br:13])[C:7]=1[N+:10]([O-:12])=[O:11])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Br:9][C:8]1[C:7]([N+:10]([O-:12])=[O:11])=[C:6]([Br:13])[NH:5][N:4]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 130072253,5-dibromo-1-propyl-4-nitro-1H-pyrazole

Product 2

HCID 13007229benzyl(5-bromo-4-nitro-2-propyl-2H-pyrazol-3-yl)amineHCID 137079943,5-Dibromo-4-nitro-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-propyl-3,5-dibromo-4-nitropyrazole (19.4 g, 62 mmol), EtOH (500 ml) and benzylamine (40 g, 373 mmol) was refluxed for 15 hours. The reaction medium was concentrated to the maximum under reduced pressure. The residue was suspended in EtOAc (100 ml ), the insoluble part was separated out by filtration and the filtrate was evaporated to dryness. The black oil obtained was purified by column chromatography (eluent: EtOAc/hexane) to give the benzyl(5-bromo-4-nitro-2-propyl-2H-pyrazol-3-yl)amine in the form of a yellow solid (9 g; 29%) from 3,5-dibromo-4-nitropyrazole.

Workup

  1. temperaturewas refluxed for 15 hours
  2. concentrationThe reaction medium was concentrated to the maximum under reduced pressure
  3. customthe insoluble part was separated out by filtration
  4. customthe filtrate was evaporated to dryness
  5. customThe black oil obtained
  6. customwas purified by column chromatography (eluent: EtOAc/hexane)

Sources & evidence

ORD record
ord-6a276ecd548e4b60acf3d70fd8f60de2
Source dataset
uspto-grants-2007_10
Patent number
US07285136B2

Reaction notes

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