Potassium Carbonate → N-Methoxy-2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorobenzamide

HRID 1531437Notes

Reaction equation

HRID 1531437 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[C:16]([Cl:17])=[C:15]([O:18][CH:19]([F:21])[F:20])[N:14]([CH3:22])[N:13]=2)=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:30][O:31][NH2:32]>C1(C)C=CC=CC=1.O>[CH3:30][O:31][NH:32][C:4](=[O:5])[C:3]1[CH:7]=[C:8]([C:12]2[C:16]([Cl:17])=[C:15]([O:18][CH:19]([F:21])[F:20])[N:14]([CH3:22])[N:13]=2)[C:9]([F:11])=[CH:10][C:2]=1[Cl:1]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 212540122-Chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorobenzoyl chloride

Product 1

HCID 21254033N-Methoxy-2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorobenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 8.4 g (22 mmol) of 2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorobenzoyl chloride in 150 ml of toluene was treated with 34 g (0.24 mol) of potassium carbonate, and 16 g (48 mmol) of a 25% strength aqueous methoxyamine hydrochloride solution was subsequently added dropwise. After the reaction mixture had been stirred for 4 hours, it was diluted with 0.5 l of water. The organic phase was then separated off, washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and finally concentrated. Yield: 8.3 g.

Workup

  1. additionwas subsequently added dropwise
  2. customThe organic phase was then separated off
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationfinally concentrated

Sources & evidence

ORD record
ord-e3d96856ada84d328de40eb23164b60e
Source dataset
uspto-grants-2001_03
Patent number
US06197973B1

Reaction notes

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