Potassium Carbonate → 4-iodo-1-(3-methyl-4-nitrobenzyl)-3-trifluoromethyl-1H-pyrazole

HRID 2243249Notes

Reaction equation

HRID 2243249 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5]Cl.[I:13][C:14]1[C:15]([C:19]([F:22])([F:21])[F:20])=[N:16][NH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[I:13][C:14]1[C:15]([C:19]([F:22])([F:21])[F:20])=[N:16][N:17]([CH2:5][C:4]2[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([CH3:1])[CH:3]=2)[CH:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 87687Alpha-chloro-3-methyl-4-nitrotolueneHCID 178506301HCID 178506301, compound

Product 1

HCID 592104224-iodo-1-(3-methyl-4-nitrobenzyl)-3-trifluoromethyl-1H-pyrazoleYield 64.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Methyl-4-nitrobenzyl chloride (0.77 g), 4-iodo-3-trifluoromethyl-1H-pyrazole (0.99 g) and potassium carbonate (0.63 g) were stirred in DMF (10 ml) at 60° C. for 1 hour. After cooling, the reaction solution was diluted with ethyl acetate and washed with water and saturated aqueous solution of sodium chloride. After drying the organic layer with magnesium sulfate, the solvent was distilled off under the reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 4-iodo-1-(3-methyl-4-nitrobenzyl)-3-trifluoromethyl-1H-pyrazole (1.0 g).

Workup

  1. temperatureAfter cooling
  2. washwashed with water and saturated aqueous solution of sodium chloride
  3. dry with materialAfter drying the organic layer with magnesium sulfate
  4. distillationthe solvent was distilled off under the reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-10123f9da2f34b419f4377e2110a3c3b
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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