Benzenesulfonyl chloride → HCID 18765369, compound

HRID 1159862Notes

Reaction equation

HRID 1159862 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[N:14]([S:26]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:28])=[O:27])[CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 2608005-Benzyloxy-6-methoxyindole

Product 1

HCID 18765369HCID 18765369, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 14798Sodium HydroxideSolvent

Procedure

To 5-benzyloxy-6-methoxyindole (5.0 g, 20 mmol), benzenesulfonyl chloride (5.2 g, 30 mmol) and tetrabutylammonium hydrogen sulfate (2.0 g, 6 mmol) DCM (200 mL) and 4M NaOH (50 mL) were added. The reaction mixture was allowed to stir at room temperature over night. The organic layer was collected and the aqueous phase was washed with DCM (2×30 mL). The combined organic layers were then washed with brine (2×50 mL). Drying, (MgSO4), filtration and evaporation afforded a brown oil. The product precipitated when adding diethyl ether. Recrystallization from MeOH afforded the title compound in 84% yield (6.55 g) as light yellow crystals. MS (ESI+) for C22H19NO4S m/z 394 (M+H)+.

Workup

  1. customThe organic layer was collected
  2. washthe aqueous phase was washed with DCM (2×30 mL)
  3. washThe combined organic layers were then washed with brine (2×50 mL)
  4. customDrying
  5. filtration, (MgSO4), filtration and evaporation
  6. customafforded a brown oil
  7. customThe product precipitated when
  8. additionadding diethyl ether
  9. customRecrystallization from MeOH

Sources & evidence

ORD record
ord-50a92435fe054cdebc3c57b3be45f1a9
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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