Experiment 5. Benzilic Acid Rearrangement: Preparation of ...
[Pages:2]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.
H N
O
O
N H
phenytoin (Dilantin)
N O NH2 carbamazapine
O HN ONO
H phenobarbital
*
Benzilic Acid Rearrangement
?Discovered in 1938 by Justus Liebig ? one of the first C-C bond migration reactions.
O
O benzil
migration!
NaOH
H2O/ethanol
O
H3O+-workup
O-Na+ HO
O OH
HO
benzilic acid
Reaction mechanism:
O -OH
O OH
O
O
bond migration, not bond breakage
O
OH
OH O
HO benzilic acid
O OH
H3O+ * R = H or C2H5
O
O
O
H OR *
O
HO
O
Chem 216 S11 Notes - Dr. Masato Koreeda Topic: _Experiment 5__ page 2 of 2.
Synthesis of Phenytoin (Dilantin)
O
O benzil
NH2 +O
NaOH
NH2 H2O/ethanol
urea
Reation Mechanism:
Date: May 10, 2011
H N
O ON
Na
H3O+ workup
H N
O
O
N H
phenytoin (Dilantin)
H
OH
NH
O
NH
H
pKa ~12
H
N
O
O
NH
H
NO N
OH H
* RO-H
H
O
ON O O
H2N
H O NO
H2N O
HO N O H2N
O
* R = H or C2H5
OR
H HO N O
H2N O
OR
NO
N
O
H
a Benzilic acid rearrangement step!
N O
N H O
H OR
N O
O
N H
H N
O ON
H
phenytoin (Dilantin)
H3O+-Workup
H N
O ON
O more acidic N-H
H
N O
N H
OR
................
................
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