Water → HCID 54898288, compound

HRID 1466387Notes

Reaction equation

HRID 1466387 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[CH:9]=[O:10].[Cl:11][C:12]1[CH:13]=[C:14]([OH:19])[CH:15]=[CH:16][C:17]=1[Cl:18].[OH-].[K+].O>CN(C=O)C>[Cl:11][C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][C:17]=1[Cl:18])[O:19][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[CH:9]=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 72583,4-DichlorophenolHCID 14797Potassium HydroxideHCID 27773975-Chloro-1,3-dimethylpyrazole-4-carboxaldehyde

Product 1

HCID 54898288HCID 54898288, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

5-chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (500.0 mg, 0.00315 mol), 3,4-dichlorophenol (565 mg, 0.00344 mol) and potassium hydroxide (265 mg, 0.00472 mol) were stirred in DMF (2.0 mL). Mixture was heated at 150° C. for 20 min using microwave. Water was added and resulting mixture was extracted with ethyl acetate. Organic layer was washed with brine twice, dried over MgSO4 and evaporated. The resulting oil was purified by column chromatography (10% to 20% ethyl acetate/heptane) to give 5-(3,4-dichlorophenoxy)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (492 mg, 54.7%) as white solid.

Workup

  1. customresulting mixture
  2. extractionwas extracted with ethyl acetate
  3. washOrganic layer was washed with brine twice
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe resulting oil was purified by column chromatography (10% to 20% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-b8ee2d04ecc44673943c6fffaf56cfe0
Source dataset
uspto-grants-2015_04
Patent number
US09000024B2

Reaction notes

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