Water → Benzoic acid, 4-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)methyleneaminooxymethyl-, 1,1-dimethylethyl ester

HRID 1905398Notes

Reaction equation

HRID 1905398 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+].Br[CH2:21][C:22]1[CH:34]=[CH:33][C:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:24][CH:23]=1.O>CS(C)=O>[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][O:16][CH2:21][C:22]2[CH:34]=[CH:33][C:25]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])=[CH:24][CH:23]=2)[C:4]([CH3:17])=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 682832N-((1,3-Dimethyl-5-phenoxy-1H-pyrazol-4-yl)methylidene)hydroxylamineHCID 11414578Tert-butyl 4-(bromomethyl)benzoate

Product 1

HCID 107760Benzoic acid, 4-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)methyleneaminooxymethyl-, 1,1-dimethylethyl esterYield 67%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
30 °C

Procedure

2.0 Grams (0.00855 mole) of 1,3-dimethyl-5-phenoxypyrazole-4-carbaldehyde oxime was dissolved in 20 ml of dimethyl sulfoxide, and after adding 0.65 g (0.0116 mole) of powdery potassium hydroxide, the resulting mixture was stirred at 30° C. for 30 minutes. To this solution was added 2.32 g (0.00855 mole) of tert-butyl 4-bromomethylbenzoate, and reaction was carried out at from 50° to 60° C. for 1 hour. 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 crude crystals. The crystals were recrystallized from methanol to obtain 2.4 g of the desired compound.

Workup

  1. additionTo this solution was added
  2. waitwas carried out at from 50° to 60° C. for 1 hour
  3. additionwas added to the reaction solution which
  4. extractionwas then extracted 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 crude crystals
  10. customThe crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-82f2521e133541019db8db5ec2ec7bdd
Source dataset
uspto-grants-1989_06
Patent number
US04843068

Reaction notes

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