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!

  • $\begingroup$ 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. $\endgroup$ – Hexacoordinate-C Oct 7 '15 at 16:36

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.


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