Potassium Carbonate → Methyl 2-chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoate

HRID 1368815Notes

Reaction equation

HRID 1368815 reaction equation
Cl.[CH2:2]([O:4][NH2:5])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[Cl:12][C:13]1[C:22]([CH:23]=O)=[C:21]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]>CO>[Cl:12][C:13]1[C:22]([CH:23]=[N:5][O:4][CH2:2][CH3:3])=[C:21]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76850O-ethylhydroxylamine hydrochlorideHCID 18517410Methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate

Product 1

HCID 54512790Methyl 2-chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoateYield 88.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.90 g (0.0195 mol) of O-ethylhydroxylamine hydrochloride and 1.35 g (0.0097 mol) of finely powdered potassium carbonate were stirred for 1 hour at room temperature in 60 ml of dry methanol, and 4.90 g (0.0177 mol) of methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate were then added. After stirring for 8 hours at room temperature, the solvent was removed, the residue was taken up in ethyl acetate and the organic phase was washed with water until neutral, dried and concentrated under reduced pressure. 5.00 g of methyl 2-chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoate were obtained. (Yield 88%).

Workup

  1. customthe solvent was removed
  2. washthe organic phase was washed with water until neutral,
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e002bb363c9643ca8f2f5247818a8978
Source dataset
uspto-grants-2003_06
Patent number
US06576596B1

Reaction notes

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