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

HRID 2243271Notes

Reaction equation

HRID 2243271 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[I:12][C:13]1[CH:14]=[N:15][NH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[I:12][C:13]1[CH:14]=[N:15][N:16]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 770224-IodopyrazoleHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 592104234-iodo-1-(3-methyl-4-nitrophenyl)-1H-pyrazoleYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-fluoro-2-nitrotoluene (2.33 g), 4-iodo-1H-pyrazole (2.91 g) and potassium carbonate (2.49 g) was heated and stirred in DMF (30 ml) at 140° C. for 4 hours. After cooling to room temperature, the reaction mixture was poured into ice water to separate out crystals. The obtained crystals were filtered, washed with water and dried, and 4-iodo-1-(3-methyl-4-nitrophenyl)-1H-pyrazole (4.60 g) was obtained.

Workup

  1. temperaturewas heated
  2. customto separate out crystals
  3. filtrationThe obtained crystals were filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-6d58418a02624c0fbca6ca95643f0663
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

Loading…