Indole → N-Tosylindole

HRID 1798017Notes

Reaction equation

HRID 1798017 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.[OH-].[K+]>C(COC)OC>[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 798IndoleHCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium Hydroxide

Product 1

HCID 10956616N-TosylindoleYield 89%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1-(p-toluenesulphonyl)indole was prepared according to the procedure described in Y. Kikugawa Synthesis 1981, 460-461, by reaction of indole with p-toluenesulphonyl chloride in the presence of potassium hydroxide in dimethoxyethane at ambient temperature for 30 minutes. Yield: 89%.

Workup

  1. customKikugawa Synthesis 1981, 460-461

Sources & evidence

ORD record
ord-9598e6ab4c82426f8ff0125526ba3cf4
Source dataset
uspto-grants-2013_01
Patent number
US08343964B2

Reaction notes

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