Benzenesulfonyl chloride → 5-Bromo-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde

HRID 1426654

反応式

HRID 1426654 の反応式
[Br:1][C:2]1[NH:6][CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=1.[H-].[Na+].[C:11]1([S:17](Cl)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCCC1.O>[Br:1][C:2]1[N:6]([S:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:19])=[O:18])[CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=1

参加物

6

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 578319835-bromo-1H-pyrrole-3-carbaldehyde

生成物 1

HCID 862328055-Bromo-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde収率 85.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-bromo-1H-pyrrole-3-carbaldehyde (3.50 g) in tetrahydrofuran (70 mL) was added sodium hydride (60% in oil, 1.21 g) at room temperature, and the mixture was stirred for 10 min. Benzenesulfonyl chloride (4.27 g) was added, and the mixture was further stirred for 1 hr, diluted with water, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→7:3) and crystallized from diisopropyl ether to give the title compound as colorless crystals (yield 5.4 g, 85%).

後処理

  1. stirringthe mixture was further stirred for 1 hr
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→7:3)
  7. customcrystallized from diisopropyl ether

出典と根拠

ORDレコード
ord-65dd15020501426ebe740c5be79d578a
出典データセット
uspto-grants-2015_01
特許番号
US08933105B2

関連ノート

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