Lithium iodide → 2-Chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoic acid

HRID 1368816Notes

Reaction equation

HRID 1368816 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[N:13][O:14][CH2:15][CH3:16])=[C:10]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[I-].[Li+]>N1C=CC=CC=1>[Cl:1][C:2]1[C:11]([CH:12]=[N:13][O:14][CH2:15][CH3:16])=[C:10]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 54512790Methyl 2-chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoate

Product 1

HCID 541651472-Chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4.37 g (0.0137 mol) of methyl 2-chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoate was slowly added dropwise to 7.29 g (0.055 mol) of lithium iodide in 50 ml of dry pyridine. After stirring for 2 hours at reflux, the reaction mixture was cooled and the solvent was removed under reduced pressure. The residue was taken up in water and adjusted to pH=1-2 with dilute hydrochloric acid. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with water, dried and concentrated under reduced pressure. 3.70 g of 2-chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoic acid were obtained. (Yield 89%).

Workup

  1. temperatureat reflux
  2. temperaturethe reaction mixture was cooled
  3. customthe solvent was removed under reduced pressure
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washthe combined organic phases were washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f7115e2b1be940028bfffa6655a5dcaf
Source dataset
uspto-grants-2003_06
Patent number
US06576596B1

Reaction notes

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