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

HRID 83755Notes

Reaction equation

HRID 83755 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-ce76ac85fd7d4def947d2fe4825603ad
Source dataset
uspto-grants-2014_09
Patent number
US08846753B2

Reaction notes

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