Sodium Hydroxide → HCID 68717174, compound

HRID 1159769Notes

Reaction equation

HRID 1159769 reaction equation
[OH-].[Na+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[S:8](Cl)(=[O:10])=[O:9].[Br:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.S1C=CC=C1S(Cl)(=O)=O>[Br:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][N:17]2[S:8]([C:4]1[S:3][CH:7]=[CH:6][CH:5]=1)(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 855182-Thiophenesulfonyl chlorideHCID 6764944-Bromoindole

Product 1

HCID 68717174HCID 68717174, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 855182-Thiophenesulfonyl chlorideCatalystHCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

Aq. 2.5M NaOH (3 mL) was added to a stirring mixture of 2-thiophenesulfonyl chloride (1.03 g, 5.61 mmol), 4-bromoindole (1.00 g, 5.10 mmol) and tetrabutylammonium hydrogen sulfate (87 mg, 0.05 mmol). The reaction was stirred over night (22 h). Additional 2-thiophenesulfonyl chloride (50 mg, 0.27 mmol) was added with continuous stirring for 3 h. The layers were allowed to separate. The organic layer was washed twice with water, dried and concentrated to get the title compound (1.67 g, 96%) as a gray solid.

Workup

  1. stirringwith continuous stirring for 3 h
  2. customto separate
  3. washThe organic layer was washed twice with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5e141919544c4c318142a5bdfaba2a6a
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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