RE: ORGLIST: Mechanism of 5,5-diphenylhydantoin

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From: RAB (rab$##$anu.edu.au)
Date: Tue Feb 22 2000 - 17:18:32 EST

This is also known as dilantin, used clinically as an antiepileptic drug.
 We used to run a a student lab making the stuff from benzil and urea. The
ref is Wilcox and Wilcox, Experimental Organic Chemistry, Prentice-Hall
1995.

The mechanism is pretty starightforward and reasonable under the basic
conditions in which the experiment is run.

Russell

*******************************************************
        Russell A. Barrow, PhD
        Department of Chemistry
        Australian National University
        Canberra, ACT 0200

        Ph: (02) 6249 3419
        Fax: (02) 6249 0760
        Web: http://chemserver.anu.edu.au/rab

*******************************************************

-----Original Message-----
From: antonio regla [SMTP:areglac$##$yahoo.com]
Sent: Wednesday, February 23, 2000 4:16 AM
To: Multiple recipients of list orglist
Subject: ORGLIST: Mechanism of 5,5-diphenylhydantoin

Dear List Members:
I am looking for the mechanism of the formation of
5,5-diphenylhidantoin from the reaction of benzil plus
urea under basic conditions. I have seen one mechanism
in an old lab manual, and it doesn't seem very likely
to me. Some of the steps seem unreasonable, I get the
feeling it is one of those mechanism proposed by
someone pressed for time. I would appreciate if
someone could point me in the right direction to find
information on a more reasonable mechanism. Thank you
all for your help.
Sincerely,
J. Antonio Regla
Chemistry Professor
School of Pharmacy
Universidad Autonoma del Estado de Morelos
Cuernavaca, Mexico
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List coordinator: Joao Aires de Sousa (jas$##$mail.fct.unl.pt)

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