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Topic: 5,5-diphenylhydantoin  (Read 9034 times)

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Offline Moz29386

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5,5-diphenylhydantoin
« on: May 04, 2010, 01:27:40 PM »
We are synthesisng 5,5-diphenylhydantoin from urea and benzil.

I need to know the mechanism for that synthesis if possible please.

I've searched the forum and this is what I found 

http://en.wikipedia.org/wiki/Benzilic_acid_rearrangement

But it doesnt help as the reaction is not complete.

Thanks.

Also; Describe a convienient method (with equations) for the synthesis of benzil. (do not include full experimental details),

Offline OC pro

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Re: 5,5-diphenylhydantoin
« Reply #1 on: May 04, 2010, 03:11:02 PM »
It´s a simple condensation. 2 Moles of water will be formed. Thats all for the mechanism.

Offline Doc Oc

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Re: 5,5-diphenylhydantoin
« Reply #2 on: May 04, 2010, 03:29:25 PM »
It's not just a simple condensation, at least one of those ketones from the benzil has to be preserved in the final product.

Take a look at this paper:  J. Chem. Educ.  1986, 63, 650.

Offline orgopete

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Re: 5,5-diphenylhydantoin
« Reply #3 on: May 05, 2010, 01:09:42 PM »
I would try writing the mechanism as an aza-benzylic acid rearrangement. First form a C=NCONH2 from one of the C=O groups. Do the rearrangement to give the urea-acid. Loss of water should give the hydantoin.
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