216%20W09-Expt%206 - OH O O OH bond migration, not bond...

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216 Winter 09 Notes - Dr. Masato Koreeda Date: March 5, 2009 Topic : _Experiment 6 __ page 1 of 2. Experiment 6. Benzilic Acid Rearrangement: Preparation of Dilantin Anticonvulsant drugs : Epilepsy : one of the most common Dilantin Sodium (phenytoin) * neurologic disorders, affecting ca. 1% of Tegretol (carbazepine) the population. Phenobarbital N H H N O O N O NH 2 HN N H O O O phenobarbital carbamazapine phenytoin (Dilantin) * 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 O migration! benzil NaOH H 2 O/ethanol Δ HO O - Na + O HO OH O benzilic acid H 3 O + -workup Reaction mechanism: O O -
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Unformatted text preview: OH O O OH bond migration, not bond breakage O O O O O H OH O H OR O O HO R = H or C 2 H 5 HO OH O benzilic acid H 3 O + * * 216 Winter 09 Notes- Dr. Masato Koreeda Date: March 5, 2009 Topic : _Experiment 6 __ page 2 of 2. Synthesis of Phenytoin (Dilantin) N H H N O O phenytoin (Dilantin) O O benzil NH 2 NH 2 O urea N H N O O Na + H 3 O + workup NaOH H 2 O/ethanol Reation Mechanism: OH R = H or C 2 H 5 * N H H N O H H pK a ~12 N H N H H O O O O O H N H 2 N O O H N H 2 N O O RO-H HO N H 2 N O O H OR HO N H 2 N O OR O N N O O H H N N O H O N H N O O N H N O O H OR N N O O H H OR N H N O O N N O O H H * H 3 O +-Workup phenytoin (Dilantin) more acidic N-H a Benzilic acid rearrangement step!...
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This note was uploaded on 01/31/2010 for the course CHEM 216 taught by Professor Nolta during the Winter '07 term at University of Michigan.

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216%20W09-Expt%206 - OH O O OH bond migration, not bond...

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