Lithium iodide → 2-Chloro-4-methylsulfonyl-3-(1,3,4-oxadiazol-2-yl)benzoic acid

HRID 1276133Notes

Reaction equation

HRID 1276133 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2[O:13][CH:14]=[N:15][N:16]=2)=[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]([C:12]2[O:13][CH:14]=[N:15][N:16]=2)=[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 22114931Methyl 2-chloro-4-methylsulfonyl-3-(1,3,4-oxadiazol-2-yl)benzoate

Product 1

HCID 221149192-Chloro-4-methylsulfonyl-3-(1,3,4-oxadiazol-2-yl)benzoic acidYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

At reflux temperature, 1.5 g (4.7 mmol) of methyl 2-chloro-4-methylsulfonyl-3-(1,3,4-oxadiazol-2-yl)benzoate in 50 ml of pyridine were added dropwise to 2.5 g (18.9 mmol) of lithium iodide in 50 ml of pyridine, and the mixture was heated under reflux until the reaction had gone to completion. The mixture was cooled, the solvent was removed, the residue was taken up in water, insoluble components were filtered off and the mixture was acidified using hydrochloric acid and extracted with methylene chloride or ethyl acetate. The combined organic phases were dried and concentrated. 1.2 g (86% of theory) of 2-chloro-4-methylsulfonyl-3-(1,3,4-oxadiazol-2-yl)benzoic acid were obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux until the reaction
  3. temperatureThe mixture was cooled
  4. customthe solvent was removed
  5. filtrationinsoluble components were filtered off
  6. extractionextracted with methylene chloride or ethyl acetate
  7. customThe combined organic phases were dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1a665b3ce2fe4362a54bdac6c45a2db8
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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