Benzenesulfonyl chloride → 1-(Phenylsulfonyl)-1,5,6,7-tetrahydro-4H-indol-4-one

HRID 2086937

Reaction equation

HRID 2086937 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[O:10])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[C:13]1([S:19]([N:1]2[C:9]3[CH2:8][CH2:7][CH2:6][C:5](=[O:10])[C:4]=3[CH:3]=[CH:2]2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 2802291,5,6,7-Tetrahydro-4H-indol-4-one

Product 1

HCID 134377091-(Phenylsulfonyl)-1,5,6,7-tetrahydro-4H-indol-4-oneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 1,5,6,7-tetrahydro-4H-indol-4-one (5.0 g, 37.0 mmol) in THF is treated portionwise with NaH (60% dispersion in mineral oil, 1.5 g, 37.0 mmol) under N2 at room temperature, stirred for 0.5 hr, treated with benzene sulfonyl chloride (4.7 ml, 37.0 mmol), stirred for 24 hr, quenched with water and diluted with EtOAc. The phases are separated. The organic phase is washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, EtOAc/hexanes, 1/1 as eluent) to afford the title product as an off-white solid, 8.72 g (85% yield), mp 108-110° C., identified by NMR and mass spectral analyses.

Workup

  1. stirringstirred for 24 hr
  2. customquenched with water
  3. additiondiluted with EtOAc
  4. customThe phases are separated
  5. washThe organic phase is washed sequentially with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue is purified by flash chromatography (silica gel, EtOAc/hexanes, 1/1 as eluent)

Sources & evidence

ORD record
ord-8094538fe8ee497da0857f8a1ee97d97
Source dataset
uspto-grants-2004_04
Patent number
US06727270B2

Linked notes

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