Indole → 1-(Phenylsulfonyl)-1H-indole

HRID 74588

Reaction equation

HRID 74588 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 mmol) sodium hydride (60%) were added to 2.0 g (17 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 mmol) benzenesulphonic acid chloride were added and 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. stirringstirred 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-54723267a08c44ae9c7b22df19a3b48f
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

Loading…