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

HRID 640644노트

반응식

HRID 640644 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-72172541233c414a8455adfdb7db18b3
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691902B2

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