Sodium Hydroxide → 5-bromo-2-(N,N-dimethylsulfamoyl)benzoic acid

HRID 2242737Notes

Reaction equation

HRID 2242737 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=C(C#N)[CH:3]=1.[OH-:16].[Na+].[O:18]1[CH2:23][CH2:22]OCC1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](=[O:10])(=[O:9])[N:11]([CH3:13])[CH3:12])=[C:22]([CH:3]=1)[C:23]([OH:18])=[O:16]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 59206579HCID 59206579, compound

Product 1

HCID 592067205-bromo-2-(N,N-dimethylsulfamoyl)benzoic acidYield 34%

Procedure

A mixture of 4-bromo-2-cyano-N,N-dimethylbenzenesulfonamide (110 mg, 0.38 mmol) and 1N aqueous NaOH (2.0 mL, 2.0 mmol) in 1,4-dioxane (2 mL) was heated at reflux. The cooled reaction mixture was washed with dichloromethane (5 mL). The aqueous layer was acidified by the addition of 1N aqueous HCl. The acidified aqueous layer was extracted with dichloromethane (2×5 mL). The combined organics were dried over Na2SO4 and evaporated to dryness to yield 5-bromo-2-(N,N-dimethylsulfamoyl)benzoic acid in 34% yield (40 mg, 0.13 mmol). ESI-MS m/z calc. 307.0, found 308.1 (M+1)+; retention time 1.13 minutes.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customThe cooled reaction mixture
  4. washwas washed with dichloromethane (5 mL)
  5. additionThe aqueous layer was acidified by the addition of 1N aqueous HCl
  6. extractionThe acidified aqueous layer was extracted with dichloromethane (2×5 mL)
  7. dry with materialThe combined organics were dried over Na2SO4
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-8dceedcb335c4f88ab7ff6cf12c3e560
Source dataset
uspto-grants-2010_03
Patent number
US07671221B2

Reaction notes

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