Sodium Hydroxide → HCID 57889163, compound

HRID 1820225Notes

Reaction equation

HRID 1820225 reaction equation
[CH3:1][S:2]([NH:5][C:6]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13]C)=[O:12])=[O:7])(=[O:4])=[O:3].[OH-].[Na+]>CO.O>[CH3:1][S:2]([NH:5][C:6]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([OH:13])=[O:12])=[O:7])(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 47269479HCID 47269479, compound

Product 1

HCID 57889163HCID 57889163, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 3-(methylsulfonylcarbamoyl)benzoate (700 mg, 2.72 mmol) was dissolved in methanol at 25° C. with stirring then 1.0 N NaOH (5.56 mL, 5.56 mmol) was added. The reaction mixture was stirred for 20 hours, diluted with water, and the methanol removed in vacuo. The aqueous was washed with diethyl ether (2×) then acidified to pH=3 with 1N HCl. The resulting solution was extracted with ethyl acetate to give 3-(methylsulfonylcarbamoyl)benzoic acid (285 mg, 1.12 mmol, 42% yield). MS found: (M+H)+=244.00.

Workup

  1. stirringThe reaction mixture was stirred for 20 hours
  2. customthe methanol removed in vacuo
  3. washThe aqueous was washed with diethyl ether (2×)
  4. extractionThe resulting solution was extracted with ethyl acetate

Sources & evidence

ORD record
ord-5ec647e65d804747810301236221d23f
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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