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216 S11-Expt 5

This document summarizes an experiment on the benzilic acid rearrangement reaction and the synthesis of the anticonvulsant drug phenytoin (Dilantin) using this reaction. The benzilic acid rearrangement is a carbon-carbon bond migration reaction discovered in 1938. It involves the rearrangement of benzilic acid to another acid under basic conditions. This reaction is utilized in the synthesis of phenytoin by reacting benzilic acid, which undergoes rearrangement, with urea to form the final product after workup. Phenytoin is an important anticonvulsant medication used to treat epilepsy, a common neurological disorder.

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103 views2 pages

216 S11-Expt 5

This document summarizes an experiment on the benzilic acid rearrangement reaction and the synthesis of the anticonvulsant drug phenytoin (Dilantin) using this reaction. The benzilic acid rearrangement is a carbon-carbon bond migration reaction discovered in 1938. It involves the rearrangement of benzilic acid to another acid under basic conditions. This reaction is utilized in the synthesis of phenytoin by reacting benzilic acid, which undergoes rearrangement, with urea to form the final product after workup. Phenytoin is an important anticonvulsant medication used to treat epilepsy, a common neurological disorder.

Uploaded by

dubstepo
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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Chem 216 S11 Notes - Dr.

Masato Koreeda
Topic: _Experiment 5__ page 1 of 2.

Date: May 10, 2011

Experiment 5. Benzilic Acid Rearrangement: Preparation of Dilantin


Anticonvulsant drugs:
Dilantin Sodium (phenytoin)*
Tegretol (carbazepine)
Phenobarbital

Epilepsy: one of the most common


neurologic disorders, affecting ca. 1% of
the population.
O

H
N
O
N
H

phenytoin (Dilantin)
*

HN

NH2

carbamazapine

N
H

phenobarbital

http://www.mentalhealth.com/drugs/f33-d05.html
http://www.pfizer.ca/our%20products/pfizer%20pharmaceutical%20group/dilantin/

Benzilic Acid Rearrangement


Discovered in 1938 by Justus Liebig one of the first C-C bond migration reactions.
O

NaOH
H2O/ethanol

benzil

H3O+-workup
O-Na+

HO

OH

HO
benzilic acid

migration!

Reaction mechanism:
O

-OH

OH

O OH
O

O H

bond migration, not bond breakage

O
O

OR *

H3O+
O
HO

OH
HO

benzilic acid
* R = H or C2H5

Chem 216 S11 Notes - Dr. Masato Koreeda


Topic: _Experiment 5__ page 2 of 2.

Date: May 10, 2011

Synthesis of Phenytoin (Dilantin)


O

NH2

O
NH2

O
benzil

NaOH

H3O+

H
N

H2O/ethanol

workup

urea

H
N
N
H

Na

phenytoin (Dilantin)

Reation Mechanism:
H
N H

OH

* RO-H

N
O

O
N H

N H

H
N

O
O

H2N

H
N

O
O

H2N

pKa ~12
* R = H or C2H5
OR
N
O

HO

O
N

N
O

H
N

HO

H2N

H2N

OR
a Benzilic acid
rearrangement step!

N
N
O

H
N

H OR

N
H

O
N

H
N

H
N

H3O+-Workup

N
H

N
H
OR

phenytoin (Dilantin)
more acidic N-H

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