Water → HCID 57194709, compound

HRID 1905407Notes

Reaction equation

HRID 1905407 reaction equation
[CH3:1][N:2]1[C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:5]([CH:14]=[N:15][OH:16])[C:4]([CH3:17])=[N:3]1.[H-].[Na+].Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2([CH3:33])[O:32][CH2:31][CH2:30][O:29]2)=[CH:24][CH:23]=1.O>O1CCOCC1>[CH3:33][C:28]1([C:25]2[CH:26]=[CH:27][C:22]([CH2:21][O:16][N:15]=[CH:14][C:5]3[C:4]([CH3:17])=[N:3][N:2]([CH3:1])[C:6]=3[O:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:23][CH:24]=2)[O:29][CH2:30][CH2:31][O:32]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 682832N-((1,3-Dimethyl-5-phenoxy-1H-pyrazol-4-yl)methylidene)hydroxylamineHCID 200354231,3-Dioxolane, 2-[4-(bromomethyl)phenyl]-2-methyl-

Product 1

HCID 57194709HCID 57194709, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.0 Gram (0.0043 mole) of 1,3-dimethyl-5-phenoxypyrazole-4-carbaldehyde oxime was dissolved in 20 ml of dioxane, and 0.14 g (0.0058 mole) of sodium hydride was added. Thereafter, 1.1 g (0.0043 mole) of 2-(4-bromomethylphenyl)-2-methyl-1,3-dioxolane was added to this solution which was then heated under reflux for 3 hours. After completion of the reaction, the reaction solution was poured into 200 ml of cold water and 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 1.3 g of the desired compound.

Workup

  1. temperaturewas then heated
  2. temperatureunder reflux for 3 hours
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with water
  7. customdried
  8. customethyl acetate was removed by evaporation
  9. customto obtain an oily product
  10. customThis oily product was column-chromatographed on silica gel

Sources & evidence

ORD record
ord-20b827804f8145dfae46a6b26fb2e1cb
Source dataset
uspto-grants-1989_06
Patent number
US04843068

Reaction notes

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