4
$\begingroup$

I want to devise the synthesis of 1,2-dinitrobenzene without producing a large amount of 1,3 or 1,4 products.

In my synthesis I have a step in which I obtain aniline. I would like to know the mechanism for protecting the amine using $\ce{CH3COCl}$ and triethylamine so I can keep it from reacting in the next step of my synthesis. I'm not really "fluent" with amine chemistry, and I have no good idea at the moment.

If you cannot make picture of mechanism, please explain it with words. I must understand!

$\endgroup$
  • $\begingroup$ For the mechanism you don't need to be fluent with amine chemistry, you just need to know a bit about carbonyl chemistry. That said I think the nitration of acetalinide gives predominantly para product. $\endgroup$ – orthocresol Oct 7 '15 at 9:19
  • $\begingroup$ After this step I make a sulfonation and after the second nitration. And finally I found my mechanism, I just made a mistake at the begining. $\endgroup$ – ParaH2 Oct 7 '15 at 16:36
5
$\begingroup$

enter image description here

The mechanism is just a regular nucleophilic attack of an amine on a carbonyl, with the triethylamine just there to pick up any loose protons at the end of the reaction.

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.