4-Toluenesulfonyl chloride → 1-(4-Methylbenzene-1-sulfonyl)-1H-indole-3-carbaldehyde

HRID 41533

Reaction equation

HRID 41533 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1.COCCOC.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>>[S:24]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1)([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25]

Participants

4

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 80711,2-DimethoxyethaneHCID 10256Indole-3-Carboxaldehyde

Product 1

HCID 7358171-(4-Methylbenzene-1-sulfonyl)-1H-indole-3-carbaldehyde

Procedure

To a solution of indole-3-carbaldehyde (4.0 g, 27.586 mmol) in 1,2-dimethoxyethane (40 mL) KOH (4.63 g, 82.758 mmol) was added at rt and stirred for 10 min. p-toluene sulfonyl chloride (5.785 g, 30.345 mmol) was added to the solution at rt and stirred for 18 h.

Workup

  1. additionwas added to the solution at rt

Sources & evidence

ORD record
ord-dc9571d6796a4b6cbea573bdf16c0c9f
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Linked notes

Loading…