Hydrochloric Acid → 4-(Methylsulfonamido)benzoic acid

HRID 1451063Notes

Reaction equation

HRID 1451063 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12]CC)=[O:11])=[CH:8][CH:7]=1)(=[O:4])=[O:3].[OH-].[Na+].Cl>>[CH3:1][S:2]([NH:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 250654ethyl 4-[(methylsulfonyl)amino]benzoate

Product 1

HCID 2506534-(Methylsulfonamido)benzoic acidYield 65%

Procedure

A mixture of ethyl 4-[(methylsulfonyl)amino]benzoate (Lumma, W. C. et al. J. Med. Chem. 1987, 30, 758-763) (2.43 g, 0.01 mol) in 1N sodium hydroxide (22 mL, 0.022 mol) was stirred at room temperature for 24 h and then at 48° C. for 24 h. The mixture was acidified with concentrated hydrochloric acid to give a white precipitate which was separated by filtration. The cake was washed with water, dried, and recrystallized with ethanol-water to give 1.4 g (65%) of the title compound as white flakes, mp 248° C.

Workup

  1. waitat 48° C. for 24 h
  2. customto give a white precipitate which
  3. customwas separated by filtration
  4. washThe cake was washed with water
  5. customdried
  6. customrecrystallized with ethanol-water

Sources & evidence

ORD record
ord-226bac93695b41d28d3620277d8eff85
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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