Imidazole → HCID 23445066, compound

HRID 433563Notes

Reaction equation

HRID 433563 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.ClC[C:10]1[CH:11]=[N:12][N:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)[CH:14]=1.[CH3:23]N(C=O)C>>[Cl:22][C:17]1[CH:16]=[C:15]([N:13]2[CH:14]=[C:10]([N:3]3[CH:7]=[CH:6][N:5]=[CH:4]3)[C:11]([CH3:23])=[N:12]2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 234450154-(Chloromethyl)-1-(3,4-dichlorophenyl)-1H-pyrazole

Product 1

HCID 23445066HCID 23445066, compoundYield 41%

Conditions

Temperature
60 °C

Procedure

Sodium hydride (0.24 g of a 55% dispersion in mineral oil, 5.5 mmol) was slowly added to a solution of imidazole (0.19 g, 2.8 mmol) in DMF: (15 ml). After 30 min at 60° C. the mixture was cooled in an ice bath and 4-chloromethyl-1-(3,4-dichloro-phenyl)-1H-pyrazole (0.50 g, 1.9 mmol) was added in one portion. The resulting mixture was stirred for 1 h at 20° C. After evaporation of the solvent the residue was dissolved in AcOEt, washed with H2O, dried (Na2SO4) and chromatographed [silica, elution with gradient CH2Cl2 to 30% (CH2Cl2/MeOH/aq. NH4OH=90:10:1)] to obtain 0.23 g (41%) of the title compound. Mp. 103-104° C. (iPr2O), MS: m/e=293 (M+H+)

Workup

  1. customAfter evaporation of the solvent the residue
  2. dissolutionwas dissolved in AcOEt
  3. washwashed with H2O
  4. dry with materialdried (Na2SO4)
  5. customchromatographed
  6. wash[silica, elution with gradient CH2Cl2 to 30% (CH2Cl2/MeOH/aq. NH4OH=90:10:1)]

Sources & evidence

ORD record
ord-609f853b4670416ea9b773cf5c7e0477
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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