Ph Ph CH3 ČH3 Methsuximide Ethosuximide Phensuximide (racemic) (racemic) (racemic) Following is a synthesis of phensuximide. CN Ph CHO + Ph KCN Ph CN CN NaOEt 1. NaOH, H,O H NÓ 2. НС, Н,о COOE 3. heat COOEt COOEL Benzal- Ethyl dehyde cyanoacetate (A) (В) (гасеmie) Ph Ph Ph CH,NH HOOC СООН ELOOC COOEt 'N' (C) (racemic) (D) (racemic) ČH3 Phensuximide (racemic)
Ph Ph CH3 ČH3 Methsuximide Ethosuximide Phensuximide (racemic) (racemic) (racemic) Following is a synthesis of phensuximide. CN Ph CHO + Ph KCN Ph CN CN NaOEt 1. NaOH, H,O H NÓ 2. НС, Н,о COOE 3. heat COOEt COOEL Benzal- Ethyl dehyde cyanoacetate (A) (В) (гасеmie) Ph Ph Ph CH,NH HOOC СООН ELOOC COOEt 'N' (C) (racemic) (D) (racemic) ČH3 Phensuximide (racemic)
Chapter22: Carbonyl Alpha-substitution Reactions
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The following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures.
Q. Show how this same synthetic strategy can be used to prepare ethosuximide and methsuximide.
![Ph
Ph
CH3
ČH3
Methsuximide
Ethosuximide
Phensuximide
(racemic)
(racemic)
(racemic)
Following is a synthesis of phensuximide.
CN
Ph CHO +
Ph
KCN
Ph
CN
CN
NaOEt
1. NaOH, H,O
H
NÓ
2. НС, Н,о
COOE 3. heat
COOEt
COOEL
Benzal-
Ethyl
dehyde cyanoacetate
(A)
(В)
(гасеmie)
Ph
Ph
Ph
CH,NH
HOOC
СООН
ELOOC
COOEt
'N'
(C)
(racemic)
(D)
(racemic)
ČH3
Phensuximide
(racemic)](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fb9589126-4bce-4246-8e7e-106818903ca0%2F6c79c194-751e-40ba-9cb1-77dabc3609ec%2Fbit0xni.jpeg&w=3840&q=75)
Transcribed Image Text:Ph
Ph
CH3
ČH3
Methsuximide
Ethosuximide
Phensuximide
(racemic)
(racemic)
(racemic)
Following is a synthesis of phensuximide.
CN
Ph CHO +
Ph
KCN
Ph
CN
CN
NaOEt
1. NaOH, H,O
H
NÓ
2. НС, Н,о
COOE 3. heat
COOEt
COOEL
Benzal-
Ethyl
dehyde cyanoacetate
(A)
(В)
(гасеmie)
Ph
Ph
Ph
CH,NH
HOOC
СООН
ELOOC
COOEt
'N'
(C)
(racemic)
(D)
(racemic)
ČH3
Phensuximide
(racemic)
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