Benzenesulfonyl chloride → HCID 10107997, compound

HRID 1159798Notes

Reaction equation

HRID 1159798 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=2[CH:3]=[CH:2]1.[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[C:12]1([S:18]([N:1]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=3[CH:3]=[CH:2]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 333703Indole-4-carboxaldehyde

Product 1

HCID 10107997HCID 10107997, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

1H-Indole-4-carbaldehyde (0.300 g, 2.01 mmol), benzensulfonyl chloride (0.47 g, 2.67 mmol) and tetrabutylammonium hydrogen sulfate (0.070 g, 0.21 mmol) were dissolved in dichloromethane (10 mL) and NaOH (413 mg, 10.33 mmol) in water (3 mL) was added. The mixture was stirred overnight and diluted with water and extracted with dichloromethane (1×). The combined organics were dried (MgSO4) and the crude product was purified with a plug of silica using 1% MeOH in dichloromethane as the eluent.

Workup

  1. extractionextracted with dichloromethane (1×)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. customthe crude product was purified with a plug of silica using 1% MeOH in dichloromethane as the eluent

Sources & evidence

ORD record
ord-7d0fd14fd4c641ab84d0b2b7bc9b0aec
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

Loading…