Benzenesulfonyl chloride → 6-Chloro-1-phenylsulfonylindole

HRID 352767Notes

Reaction equation

HRID 352767 reaction equation
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

Participants

7

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8058HexaneHCID 871116-ChloroindoleHCID 178418339Butyllithium

Product 1

HCID 5068286-Chloro-1-phenylsulfonylindole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6226b0b864144981946253a112647c1f
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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