2,4-Dichlorobenzyl chloride → HCID 22388505, compound

HRID 1072847Notes

Reaction equation

HRID 1072847 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH3:14])=[N:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].[H-].[Na+].[Cl:17][C:18]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:19]=1[CH2:20]Cl>CN(C)C=O>[Cl:17][C:18]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:19]=1[CH2:20][N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:13]=2)[C:9]([CH3:14])=[N:10]1

Participants

5

Reactant 3

HCID 72122,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 178497281HCID 178497281, compound

Product 1

HCID 22388505HCID 22388505, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

6-(Methoxycarbonyl)-3-methyl-1H-indazole (0.40 g, 2.1 mmol) was dissolved in dimethylformamide (15 ml) and the mixture was ice-cooled. Sodium hydride (85 mg, 60% suspension in oil, 2.1 mmol as NaH) was added and the mixture was stirred at 0° C. for 30 min. 2,4-Dichlorobenzyl chloride (0.45 g, 2.31 mmol) was added and the mixture was stirred at room temperature for 18 hr. The reaction mixture was extracted with ethyl acetate/water. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The drying agent was filtered off and the filtrate was concentrated under reduced pressure. The obtained crystalline residue was separated and purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1) to give the objective compound (0.54 g, 74%) as colorless crystals.

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred at room temperature for 18 hr
  3. extractionThe reaction mixture was extracted with ethyl acetate/water
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe drying agent was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained crystalline residue was separated
  9. custompurified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-d2a2c95c5d7a46c49a3d93122cd994a0
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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