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

HRID 640644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 640644
[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]

Komponenten

4

Edukt 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 592065794-bromo-2-cyano-N,N-dimethylbenzenesulfonamide

Produkt 1

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

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-72172541233c414a8455adfdb7db18b3
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691902B2

Notizen zur Reaktion

Wird geladen…