MKSStal
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Sulfonamide hydrolysis
I want to ask if it is possible or hard to hydrolyse sulfonamides? Because for me reactions of NaOH with p-toluenesulfonamide (self prepared from
chloramine T) gave no ammonia and NaOH with sulfamic acid despite great heat of neutralization reaction made only a little ammonia gas (slight odour
and universal indicator paper turned blue) compared to amide with carbonyle group (I probably used urea). Is S-N bond so persistent?
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Boffis
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Sulphamic acid react with nitrous acid (or sodium nitrite) to give sulphuric acid/sulphate ions plus nitrogen and water. I don't know if this would
work with aromatic sulphonamides but I don't see why not; certainly worth a try. You would need to add an acid to the sodium nitrite sulphonide
mixture since toluenesulphonamide is not acidic in itself. The liberation of nitrogen should indicate that a reaction is taking place.
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AvBaeyer
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A simple google search "hydrolysis of sulfonamides" will give you plenty of information. Great how that works.
AvB
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