Hydrochloric Acid → 1-(benzenesulfonyl)-1H-indole-5-carbaldehyde

HRID 2181193Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>O1CCCC1>[C:14]1([S:20]([N:1]2[C:9]3[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

15.8 g Indole-5-carboxaldehyde were dissolved in 300 ml tetrahydrofuran and cooled to 0° C. Then, 5.12 g sodium hydride (55% in mineral oil) were added in small portions followed by slow, trop by trop addition of 15.2 ml of benzenesulfonyl chloride. The reaction mixture was then warmed up to ambient temperature and stirring continued for 16 hours. It was then poured onto ice, neutralized to pH 4 with HCl (1N) and extracted 3 times with ethyl acetate. The combined organic phases were washed with water, dried over magnesium sulfate and evaporated to give a crude product which was purified by chromatography (silicagel, eluent: gradient of n-heptane/ethyl acetate) to yield 4.09 g 1-benzenesulfonyl-1H-indole-5-carbaldehyde as rose solid.

Workup

temperatureThe reaction mixture was then warmed up to ambient temperature
additionIt was then poured onto ice
extractionextracted 3 times with ethyl acetate
washThe combined organic phases were washed with water
dry with materialdried over magnesium sulfate
customevaporated
customto give a crude product which
customwas purified by chromatography (silicagel, eluent: gradient of n-heptane/ethyl acetate)

Sources & evidence

ORD record: ord-8ca47aa124fd4ca6b10f259b16c412ca
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06890947B2

Reaction notes

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