Benzenesulfonyl chloride → HCID 68694614, compound

HRID 1191668Notes

Reaction equation

HRID 1191668 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:7]2.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>CN(C)C=O.O>[C:19]1([S:25]([N:9]2[C:10]3[C:6](=[CH:5][C:4]([Br:3])=[CH:12][CH:11]=3)[CH:7]=[C:8]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 8389235-bromo-2-phenyl-1H-indole

Product 1

HCID 68694614HCID 68694614, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (in oil, minimum 55%, 801 mg) in N,N-dimethylformamide (30 mL) was added dropwise a solution of 5-bromo-2-phenylindole (3.33 g) in N,N-dimethylformamide (30 mL) under cooling with ice and under an argon atmosphere, and the mixture was stirred at room temperature for one hour and a half. Then benzenesulfonyl chloride (1.88 mL) was added dropwise and the stirring was continued for additional 17 hours. A saturated aqueous ammonium chloride solution and water were added to the reaction mixture and this resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (1.87 g).

Workup

  1. temperatureunder cooling with ice and under an argon atmosphere
  2. waitthe stirring was continued for additional 17 hours
  3. extractionthis resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-df4fd8ff5cf040ce9c4336ff57ba8f22
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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