Bromine → 4′-Bromo-5′-(difluoromethoxy)-1′-methyl-4-nitro[1,3′-bi-1H-pyrazol]-5-amine

HRID 362640Notes

Reaction equation

HRID 362640 reaction equation
[Br:1]Br.[NH2:3][C:4]1[N:8]([C:9]2[CH:13]=[C:12]([O:14][CH:15]([F:17])[F:16])[N:11]([CH3:18])[N:10]=2)[N:7]=[CH:6][C:5]=1[N+:19]([O-:21])=[O:20]>C(O)(=O)C>[NH2:3][C:4]1[N:8]([C:9]2[C:13]([Br:1])=[C:12]([O:14][CH:15]([F:16])[F:17])[N:11]([CH3:18])[N:10]=2)[N:7]=[CH:6][C:5]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 24408BromineHCID 15767491HCID 15767491, compound

Product 1

HCID 157674924′-Bromo-5′-(difluoromethoxy)-1′-methyl-4-nitro[1,3′-bi-1H-pyrazol]-5-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8.3 g (0.052 mol) Bromine was added dropwise at room temperature to 13 g (0.047 mol) 5-amino-4-nitro-1-(5-difluoromethoxy-1-methyl-3-pyrazolyl)pyrazole dissolved in 260 ml acetic acid and the mixture stirred for 30 minutes. It was then concentrated and the residue taken up in the ethyl acetate and shaken with 5% aqueous sodium hydrogen carbonate. The phases were separated and the organic phase dried over magnesium sulfate. This was concentrated and the residue purified by silica gel column chromatography (hexane/ethyl acetate 3:1).

Workup

  1. concentrationIt was then concentrated
  2. stirringshaken with 5% aqueous sodium hydrogen carbonate
  3. customThe phases were separated
  4. dry with materialthe organic phase dried over magnesium sulfate
  5. concentrationThis was concentrated
  6. customthe residue purified by silica gel column chromatography (hexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-84babfbe6bff416ea8d134af4062740e
Source dataset
uspto-grants-1999_02
Patent number
US05869686

Reaction notes

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