Benzenesulfonyl chloride → 6-Chloro-1-phenylsulfonylindole

HRID 352767ノート

反応式

HRID 352767 の反応式
C([Li])CCC.CCCCCC.[Cl:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[CH:18][NH:19]2)=[CH:15][CH:14]=1.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1.O>[Cl:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[CH:18][N:19]2[S:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:30])=[O:29])=[CH:15][CH:14]=1

参加物

7

反応物 4

HCID 7369Benzenesulfonyl chlorideHCID 8058HexaneHCID 871116-ChloroindoleHCID 178418339Butyllithium

生成物 1

HCID 5068286-Chloro-1-phenylsulfonylindole

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-40 °C

実験手順

At −78° C., n-butyl lithium (a 1.61M hexane solution, 3.34 ml) was added to a solution of 6-chloroindole (777 mg) in tetrahydrofuran (25 ml), followed by heating to −40° C. over 1 hour. The reaction mixture was cooled back to −78° C. and added with benzenesulfonyl chloride (867 μl). The resulting mixture was heated to room temperature over 3 hours. Water was added to the reaction mixture, followed by extraction with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (40 g of silica gel, hexane:ethyl acetate=5:7). The white solid so obtained was recrystallized from ethanol, whereby the title compound (826 mg, 55%) was obtained as a white solid.

後処理

  1. temperatureThe reaction mixture was cooled back to −78° C.
  2. temperatureThe resulting mixture was heated to room temperature over 3 hours
  3. extractionfollowed by extraction with dichloromethane
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column (40 g of silica gel, hexane:ethyl acetate=5:7)
  7. customThe white solid so obtained
  8. customwas recrystallized from ethanol, whereby the title compound (826 mg, 55%)
  9. customwas obtained as a white solid

出典と根拠

ORDレコード
ord-6226b0b864144981946253a112647c1f
出典データセット
uspto-grants-2004_06
特許番号
US06747023B1

反応ノート

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