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Topic: Synthesis of Sulfanilamide from Aniline  (Read 9975 times)

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Synthesis of Sulfanilamide from Aniline
« on: May 15, 2011, 09:25:14 AM »
some questions regarding the synthesis:

1)   Why is an acetyl group added to aniline (making acetanilide) and then removed to regenerate the amine group in sulfanilamide.


2)   Acetic anhydride, like any anhydride, reacts with water to for a carboxylic acid. How then is it possible to carry out an acetylation in aqueos solution?
what is the purpose of the HCl and the sodium acetate in this reaction?

3)   What happens when p-acetaminobenzenesulfonyl chloride is allowed to stand for some time in contact with water?

(i'll get a pic of the rxn up soon)
we carried out this synthisis in the lab so if you need to know any of the conditions or reagents just ask :)

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Re: Synthesis of Sulfanilamide from Aniline
« Reply #1 on: May 15, 2011, 04:51:04 PM »
here's the synthesis rxn.
we did it as 4 steps.


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Re: Synthesis of Sulfanilamide from Aniline
« Reply #2 on: May 15, 2011, 05:12:56 PM »
btw can anyone help me balance step 3-4?
p-acetamidobenzenesufonamide - sulfanilimide
C8H10N2O3S    ---->    C6H8N202S

HCl and soduim acetate were also used so they might play a part in the above eqn (unlikely both would be catalysts?)  i just cant seem to work it out.

well unless i have C8H10N2O3S    ---->    C6H8N202S + C2H20 but i'm not sure if C2H20 is a likely product in this?

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