Indole → 1-(Phenylsulfonyl)-1H-indole

HRID 1640261Notes

Reaction equation

HRID 1640261 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>C1COCC1.CCOC(C)=O>[C:12]1([S:18]([N:3]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 798IndoleHCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydride

Product 1

HCID 3150171-(Phenylsulfonyl)-1H-indole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.89 g (22.2 mmol) sodium hydride (60%) were added to 2.0 g (17.1 mmol) indole in 30 mL THF while cooling with an ice bath and the mixture was stirred for 15 min at this temperature. Then 2.2 mL (17.0 mmol) benzenesulphonic acid chloride were added and the mixture was stirred overnight at RT. The reaction mixture was combined with water and EtOAc and extracted several times with EtOAc. The combined organic phases were dried on sodium sulphate and evaporated down.

Workup

  1. temperaturewhile cooling with an ice bath
  2. stirringthe mixture was stirred overnight at RT
  3. extractionextracted several times with EtOAc
  4. customThe combined organic phases were dried on sodium sulphate
  5. customevaporated down

Sources & evidence

ORD record
ord-a2f83a067f36495c97d0edecb07aea0f
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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