August 09, 2020, 01:52:16 PM
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Topic: Friedel craft acylation of phenylenediamide  (Read 3847 times)

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Offline alireza.shimi

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Friedel craft acylation of phenylenediamide
« on: February 08, 2012, 04:37:17 AM »
Hi all.

To achieve desired di-acylated molecule, I need to do friedel-crafts acylation reaction on para (or meta)-phenylenediamide which obtained from reaction of corresponding phenylenediamine with chloroacetylchlorid. Some attempts with chloroacetylchlorid as acylating agent and FeCl3, BF3, ZrOCl2 and  AlCl3 as Lewis acid and CH2Cl2, DMF as solvent were unsuccessful. Even with 48 h refluxing condition only initial diamide was recovered. However with use of 10 fold AlCl3 respect to the amide  and refluxing for 3 day in acetonitrile major of amide was converted to tree more polar products (based on TLC) which IR and H-NMR data of major product (90%) don't confirm desired product and refer to unrecognizable compound (probably ring closing product).


I will be grateful of you.
If anyone Can help me and suppose where is the problem?
Whether it is possible under Friedel-crafts process diamides to be di-acylated?
How could I do it?

Offline Honclbrif

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Re: Friedel craft acylation of phenylenediamide
« Reply #1 on: February 08, 2012, 12:51:05 PM »
I'm a little unclear on what you're trying to do here. Are you trying to further acylate the aromatic ring of di-N-acyl phenylenediamine, or are you trying to acylate the amines of phenylenediamine free base?
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Offline alireza.shimi

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Re: Friedel craft acylation of phenylenediamide
« Reply #2 on: February 09, 2012, 01:58:16 AM »
I'm a little unclear on what you're trying to do here. Are you trying to further acylate the aromatic ring of di-N-acyl phenylenediamine, or are you trying to acylate the amines of phenylenediamine free base?

The amine groups already converted to amide but in this point I decided to introduce two acyl groups in the aromatic ring at orto- position.

Offline Arctic-Nation

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Re: Friedel craft acylation of phenylenediamide
« Reply #3 on: February 12, 2012, 05:46:25 AM »
I have no experience with oxindoles, but maybe you can try Buchwald's procedure.

But even if you can get the reaction to work, I'm not sure you won't run into regioselectivity problems.

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