Sodium Hydroxide → 1-Methyl-1H-pyrazol-5-yl 2,4-dichlorobenzoate

HRID 637592Notes

Reaction equation

HRID 637592 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[C:8]([OH:9])=[CH:7][CH:6]=[N:5]1.[Cl:10][C:11]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14]>C(Cl)(Cl)Cl>[CH3:3][N:4]1[C:8]([O:9][C:13](=[O:14])[C:12]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:11]=2[Cl:10])=[CH:7][CH:6]=[N:5]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 666452,4-Dichlorobenzoyl chlorideHCID 178481816HCID 178481816, compound

Product 1

HCID 155907271-Methyl-1H-pyrazol-5-yl 2,4-dichlorobenzoateYield 86.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
10 °C

Procedure

In 30 ml of an aqueous solution containing 4.0 g (0.1 mol) of sodium hydroxide was dissolved 9.8 g (0.1 mol) of 1-methyl-5-hydroxypyrazole at room temperature. To the resulting aqueous solution maintained at 10° C. was added dropwise a solution prepared from 23.0 g (0.11 mol) of 2,4-dichlorobenzoyl chloride and 100 ml of chloroform with stirring over 1 hour, followed by additional stirring for 2 hours at a temperature below about 20° C. Then the chloroform layer was separated and washed successively with water, 5% aqueous sodium bicarbonate and saturated brine and, after drying, solvent was distilled off under reduced pressure to give 23.5 g of 1-methyl-5-(2,4-dichlorobenzoyloxy)-pyrazole (yield: 86%).

Workup

  1. additionwas added dropwise a solution
  2. stirringby additional stirring for 2 hours at a temperature below about 20° C
  3. customThen the chloroform layer was separated
  4. washwashed successively with water, 5% aqueous sodium bicarbonate and saturated brine
  5. customafter drying
  6. distillationsolvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-08d8177d301540758aa527530ff2fd85
Source dataset
uspto-grants-1985_12
Patent number
US04557753

Reaction notes

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