Potassium Carbonate → 2-Chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoic acid

HRID 1368814Notes

Reaction equation

HRID 1368814 reaction equation
Cl.[CH2:2]([O:4][NH2:5])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[Cl:12][C:13]1[C:21]([CH:22]=O)=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]>CO>[Cl:12][C:13]1[C:21]([CH:22]=[N:5][O:4][CH2:2][CH3:3])=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76850O-ethylhydroxylamine hydrochlorideHCID 185174222-Chloro-3-formyl-4-methylsulfonylbenzoic acid

Product 1

HCID 541651472-Chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoic acidYield 78.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.63 g (0.017 mol) of O-ethylhydroxylamine hydrochloride and 1.15 g (0.0085 mol) of finely powdered potassium carbonate were stirred for 1 hour in 60 ml of dry methanol. 4.00 g (0.015 mol) of 2-chloro-3-formyl-4-methylsulfonylbenzoic acid in 40 ml of methanol were then added. After stirring for 12 hours at room temperature, the solvent was removed, the residue was taken up in ethyl acetate and the organic phase was washed four times with water. After drying and removal of the solvent by distillation, 3.60 g of 2-chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoic acid (78% yield) were obtained.

Workup

  1. customthe solvent was removed
  2. washthe organic phase was washed four times with water
  3. customAfter drying
  4. customremoval of the solvent
  5. distillationby distillation

Sources & evidence

ORD record
ord-8cede7a66126465d97f5c16195d32a9e
Source dataset
uspto-grants-2003_06
Patent number
US06576596B1

Reaction notes

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