The following three derivatives of succinimide are anticonvulsants and have found use in the treatment of epilepsy, particularly petit mal seizures.PhPh`N'`N'ČH3ČH3MethsuximideEthosuximidePhensuximideFollowing is a synthesis of phensuximide.CNPhCNPhCN1. NaOH, H2O2. HC, Н20NaOEtKCNPh-CHOcOOEtHcOOEtNCCOOEt3. НeatEthylcyanoacetate(A)(B)BenzaldehydePhPhPhCH;NH2НООССООНEt0oCCOOEt`N'(C)(D)ČH3PhensuximideMethsuximide is formed by a similar pathway to that shown for phensuximide. Draw the structure of the compound that reacts with ethyl cyanoacetate in the synthesis ofmethsuximide.

Starting from benzaldehyde we get phensuccimide that has a phenyl group and an H at carbon alpha to…

The following three derivatives of succinimide are anticonvulsants and have found use in the treatment of epilepsy, particularly petit mal seizures. Ph Ph O: '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. HCI, H2O 3. Нeat COOET COOEt NC COOE. Ethyl cyanoacetate (A) (B) Benzaldehyde Ph Ph Ph CH;NH2 НООС COOH Et0OC COOEt (C) (D) CH3 Phensuximide Methsuximide is formed by a similar pathway to that shown for phensuximide. Draw the structure of the compound that reacts with ethyl cyanoacetate in the synthesis of methsuximide.

The following three derivatives of succinimide are anticonvulsants and have found use in the treatment of epilepsy, particularly petit mal seizures. Ph Ph O: '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. HCI, H2O 3. Нeat COOET COOEt NC COOE. Ethyl cyanoacetate (A) (B) Benzaldehyde Ph Ph Ph CH;NH2 НООС COOH Et0OC COOEt (C) (D) CH3 Phensuximide Methsuximide is formed by a similar pathway to that shown for phensuximide. Draw the structure of the compound that reacts with ethyl cyanoacetate in the synthesis of methsuximide.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter24: Amines And Heterocycles

Section24.SE: Something Extra

Problem 78AP

See similar textbooks

Similar questions

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.
Triethylenemelamine (TEM) is an antitumor agent. Its activity is due to its ability to cross-link DNA. a. Explain why it can be used only under slightly acidic conditions. b. Explain why it can cross-link DNA.
1. Biogenic Amines are inactivated primarily by a. Sulfonation b. Glucoronidation c. Aromatic hydroxylation d. Methylation 2. A drug can exert its pharmacological effect only if it is a. Protein bound b. Protein unbound c. Free drug d. Both B & C e. Both A & C 3. In order for the drug to be ready and available for absorption, it must be release first from its dosage form with the exception of: a. Capsule b. Tablet c. Solution d. Suspension 4. All of the following are true, except a. Solubility increase with decrease particle size b. Solubility increase with increase surface area c. Solubility increase with increase particle size d. Solubility decrease with decrease surface area 5. The rate in which the drug appears in the bloodstream is also known as a. Half-life b. Potency c. Bioavailability d. Area under the curve
2 Draw structures to correspond with the following common and systematic names:(a) phenyl formate (b) cyclohexyl benzoate (c) cyclopentyl phenylacetate(d) N-butylacetamide (e) N,N-dimethylformamide (f) benzoic propionic anhydride(g) benzamide (h) g-hydroxyvaleronitrile (i) a-bromobutyryl chloride(j) b@butyrolactone (k) phenyl isocyanate (l) cyclobutyl ethyl carbonate(m) d@caprolactam (n) trichloroacetic anhydride (o) ethyl N-methyl carbamate
ripelennamine is a histamine H1 antagonist with low sedative action but frequent gastrointestinal irritation. It is used to treat asthma; hay fever; urticaria; and rhinitis. Based on biotransformations discussed in class, draw the structures of 3 possible metabolites of tripelennamine.
Which of the following reactions represents the most likely reaction of naproxen with water? a.) C14H14O3(aq) + H2O(l) ⇄C14H13O3-(aq) + OH-(aq) b.) C14H14O3(aq) + H2O(l) ⇄C14H15O3+(aq) + OH-(aq) c.) C14H14O3(aq) + H2O(l) ⇄ C14H13O3-(aq) + H3O+(aq) d.) C14H14O3(aq) + H2O(l) ⇄C14H15O3+(aq) + H3O+(aq)
Several compounds have been found to inhibit -lactamase, and drugs based on these compounds can be taken in combination with penicillins and cephalosporins to restore their effectiveness when resistance is known to be a problem. The commonly prescribed formulation called Augmentin is a combination of the -lactamase inhibitor shown below with amoxicillin (shown above). It is used to treat childhood ear infections when resistance is suspected, and many kids know it as the white liquid that tastes like bananas. Which of the statements below are true statements? 1. The stereochemistry of the fusion between the four-and five-membered rings in the inhibitor and amoxicillin are different. 2. The inhibitor possesses enol ether and allylic alcohol functional groups while the antibiotic possesses a phenol and a secondary amide functional group. 3. Neither the inhibitor nor the antibiotic contains strained rings. 4. Both 1 and 2 are true.