Benzenesulfonyl chloride → 4-(2-Chloroethoxy)-1-(phenylsulfonyl)-1H-Indole

HRID 49990Notes

Reaction equation

HRID 49990 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2.[H-].[Na+].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])(O)=O.[Na+]>O1CCCC1.CCOC(C)=O>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[S:22]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:24])=[O:23]

Participants

7

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 106317214-(2-chloroethoxy)-1H-indole

Product 1

HCID 104047244-(2-Chloroethoxy)-1-(phenylsulfonyl)-1H-Indole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 4-(2-chloroethoxy)-1H-indole (3.4 g, 17.4 mmol) in tetrahydrofuran is treated with sodium hydride (60% in mineral oil, 1.04 g, 26.1 mmol) under nitrogen at room temperature, stirred for 30 minutes, treated with benzenesulfonyl chloride (3.4 mL, 26.1 mmol) stirred at room temperature overnight and treated with saturated NaHCO3 and EtOAc. The resultant phases are separated. The aqueous phase is extracted with EtOAc and the combined organic phase is washed sequentially with H2O and saturated NaCl, dried over MgSO4 and concentrated in vacuo to give a residue. The residue is purified by flash chromatography (silica gel, EtOAc/hexane: 2/8) to give the title compound as an off-white solid, 4.94 g (86%), mp 85-87° C., identified by NMR and mass spectral analyses.

Workup

  1. stirringstirred at room temperature overnight
  2. customThe resultant phases are separated
  3. extractionThe aqueous phase is extracted with EtOAc
  4. washthe combined organic phase is washed sequentially with H2O and saturated NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a residue
  8. customThe residue is purified by flash chromatography (silica gel, EtOAc/hexane: 2/8)

Sources & evidence

ORD record
ord-5321d9533f8d45ea99554516fa6493d4
Source dataset
uspto-grants-2004_03
Patent number
US06710069B2

Reaction notes

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