Benzenesulfonyl chloride → HCID 18765369, compound

HRID 2423131Notes

Reaction equation

HRID 2423131 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[NH:16][CH:15]=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[N:16]([S:28]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:30])=[O:29])[CH:15]=[CH:14]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 2608005-Benzyloxy-6-methoxyindole

Product 1

HCID 18765369HCID 18765369, compoundYield 71.7%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

3 M NaOH (5 mL, 15 mmol) was added to a solution of 5-(benzyloxy)-6-methoxy-indole (1.0 g, 3.9 mmol), tetrabutylammonium hydrogen sulfate (0.400 g, 1.18 mmol) and benzenesulfonyl chloride (1.04 g, 5.92 mmol) in DCM (25 mL). The mixture was stirred overnight at room temperature and diluted with DCM and water. The organic phase was washed with water (1×), dried (MgSO4) and evaporated. The crude product was purified through a plug of silica gel using DCM as the eluent to give the title compound (1.1 g) as a white solid. MS m/z 394 [M+H]+.

Workup

  1. washThe organic phase was washed with water (1×)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe crude product was purified through a plug of silica gel

Sources & evidence

ORD record
ord-c310c27a59d042328cd8f50961b437f0
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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