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

HRID 83755ノート

反応式

HRID 83755 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ce76ac85fd7d4def947d2fe4825603ad
出典データセット
uspto-grants-2014_09
特許番号
US08846753B2

反応ノート

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