Dimethyl Sulfoxide → 2-[(1,3-Dimethyl-5-phenoxypyrazol-4-yl)methyleneaminooxy]ethyl benzoate

HRID 1905409Notes

Reaction equation

HRID 1905409 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.[OH-].[K+].CS(C)=O.[C:24]([O:32][CH2:33][CH2:34]Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[C:24]([O:32][CH2:33][CH2:34][O:16][N:15]=[CH:14][C:5]1[C:4]([CH3:17])=[N:3][N:2]([CH3:1])[C:6]=1[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 959522-ChloroethylbenzoateHCID 682832N-((1,3-Dimethyl-5-phenoxy-1H-pyrazol-4-yl)methylidene)hydroxylamine

Product 1

HCID 539442412-[(1,3-Dimethyl-5-phenoxypyrazol-4-yl)methyleneaminooxy]ethyl benzoateYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.0 Gram (0.0043 mole) of 1,3-dimethyl-5-phenoxypyrazole-4-carbaldehyde oxime and 0.3 g (0.0054 mole) of powdery potassium hydroxide were added to 20 ml of dimethyl sulfoxide, and the resulting mixture was stirred for 30 minutes. To this solution was added 0.8 g (0.0043 mole) of 2-chloroethyl benzoate, and reaction was carried out at from 40° to 50° C. for 3 hours. After completion of the reaction, water was added to the reaction solution which was then extracted with ethyl acetate. The ethyl acetate 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. additionTo this solution was added
  2. waitwas carried out at from 40° to 50° C. for 3 hours
  3. additionwas added to the reaction solution which
  4. extractionwas then extracted with ethyl acetate
  5. washThe ethyl acetate was 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-c9b362c9cd3944b3937c1ba00b5d11d0
Source dataset
uspto-grants-1989_06
Patent number
US04843068

Reaction notes

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