The following three derivatives of succinimide are anticonvulsants and have found use in the treatment of epilepsy, particularly petit mal seizures. Ph Ph ČH3 Methsuximide Ethosuximide Phensuximide Following is a synthesis of phensuximide. CN Ph CN Ph CN NaOEt KCN 1. NaOH, H2O Ph-CHO 2. HCI, Н-О 3. Нeat COOEt COOEt NC COOET Ethyl cyanoacetate (A) (B) Benzaldehyde Ph Ph Ph CH;NH2 HOOC COOH EtOOC COOEt (C) (D) CH3 Phensuximide In the conversion of (B) to (C), draw the structure of the product of step 1.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter27: Biomolecules: Lipids
Section27.SE: Something Extra
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The following three derivatives of succinimide are anticonvulsants and have found use in the treatment of epilepsy, particularly petit mal seizures.
Ph.
Ph
`N'
ČH3
ČH3
Methsuximide
Ethosuximide
Phensuximide
Following is a synthesis of phensuximide.
CN
Ph
CN
Ph
CN
NaOEt
KCN
1. NaOH, H2O
Ph-CHO
2. HС, Н20
COOET
H
cOOEt
NC
COOEt
3. Нeat
Ethyl
cyanoacetate
(A)
(B)
Benzaldehyde
Ph.
Ph
Ph
CH3NH2
НООС
СООН
EtOOC
COOET
`N'
(C)
(D)
ČH3
Phensuximide
In the conversion of (B) to (C), draw the structure of the product of step 1.
Transcribed Image Text:The following three derivatives of succinimide are anticonvulsants and have found use in the treatment of epilepsy, particularly petit mal seizures. Ph. Ph `N' ČH3 ČH3 Methsuximide Ethosuximide Phensuximide Following is a synthesis of phensuximide. CN Ph CN Ph CN NaOEt KCN 1. NaOH, H2O Ph-CHO 2. HС, Н20 COOET H cOOEt NC COOEt 3. Нeat Ethyl cyanoacetate (A) (B) Benzaldehyde Ph. Ph Ph CH3NH2 НООС СООН EtOOC COOET `N' (C) (D) ČH3 Phensuximide In the conversion of (B) to (C), draw the structure of the product of step 1.
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