Water → HCID 57296520, compound

HRID 1905399Notes

Reaction equation

HRID 1905399 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[N:11]([CH3:12])[N:10]=[C:9]([CH3:13])[C:8]=2[CH:14]=[N:15][OH:16])=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:22][C:23]1[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26].O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[N:11]([CH3:12])[N:10]=[C:9]([CH3:13])[C:8]=2[CH:14]=[N:15][O:16][CH2:22][C:23]2[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=2[C:25]([O:27][CH3:28])=[O:26])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 12148555-(4-Chlorophenoxy)-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde oximeHCID 2734813Methyl 2-(bromomethyl)benzoate

Product 1

HCID 57296520HCID 57296520, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.0 Grams (0.00755 mole) of 5-(4-chlorophenoxy)-1,3-dimethyl-pyrazole-4-carbaldehyde oxime was dissolved in 20 ml of dimethylformamide, and after adding 0.5 g (0.0125 mole) of powdery sodium hydroxide, the resulting mixture was thoroughly stirred. To this solution was added 1.73 g (0.00755 mole) of methyl 2-bromomethylbenzoate, and reaction was carried out at from 70° to 80° C. for 5 hours. After completion of the reaction, water was added to the reaction solution which was then extracted with ethyl acetate. The ethyl acetate extract was washed with water and dried, and ethyl acetate was removed by evaporation to obtain an oily product. This oily product was column-chromatographed on silica gel to obtain 2.0 g cf the desired compound.

Workup

  1. additionTo this solution was added
  2. additionwas added to the reaction solution which
  3. extractionwas then extracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with water
  6. customdried
  7. customethyl acetate was removed by evaporation
  8. customto obtain an oily product
  9. customThis oily product was column-chromatographed on silica gel

Sources & evidence

ORD record
ord-8e2f7b376ba54bddb235da80c47af322
Source dataset
uspto-grants-1989_06
Patent number
US04843068

Reaction notes

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