Allyl bromide → HCID 18689508, compound

HRID 1871875Notes

Reaction equation

HRID 1871875 reaction equation
Br[CH2:2][CH:3]=[CH2:4].[NH2:5][C:6]1[N:10]([C:11]2[C:16]([Cl:17])=[CH:15][C:14]([C:18]([F:21])([F:20])[F:19])=[CH:13][N:12]=2)[N:9]=[CH:8][C:7]=1[N+:22]([O-:24])=[O:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:2]([NH:5][C:6]1[N:10]([C:11]2[C:16]([Cl:17])=[CH:15][C:14]([C:18]([F:20])([F:21])[F:19])=[CH:13][N:12]=2)[N:9]=[CH:8][C:7]=1[N+:22]([O-:24])=[O:23])[CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 13755224HCID 13755224, compound

Product 1

HCID 18689508HCID 18689508, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1.0 g (0.0082 mol) of 3-bromopropene was added with stirring to a mixture of 2.3 g (0.0075 mol) of 5-amino-4-nitro-1-(3-chloro-5-trifluoromethyl-2-pyridyl)pyrazole, 0.6 g (0.0041 mol) of potassium carbonate and 50 ml of dimethylformamide and it was stirred at 100° C. for 2 hours. After cooling, it was concentrated under reduced pressure and the residue was partitioned between water and methylene chloride. The organic phase was dried, filtered off with suction through silica gel and concentrated, 1.6 g (61.3% of theory) of the title compound being obtained as a viscous resin. After chromatographing on silica gel and concentrating, colorless crystals of m.p. 94-95° C. were obtained (Active Compound Example No. 9.003).

Workup

  1. temperatureAfter cooling
  2. concentrationit was concentrated under reduced pressure
  3. customthe residue was partitioned between water and methylene chloride
  4. customThe organic phase was dried
  5. filtrationfiltered off with suction through silica gel
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d8f69e6bf1b74a09a2af677b2e70f4be
Source dataset
uspto-grants-2000_08
Patent number
US06107253

Reaction notes

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