Show how you might bring about formation of the amide in Step 2. A newer generation of antipsychotics, among them clozapine, are now used to treatthe symptoms of schizophrenia. These drugs are more effective than earlier drugsin improving patient response in the areas of social withdrawal, apathy, memory,comprehension, and judgment. They also produce fewer side effects such as seizuresand tardive dyskinesia (involuntary body movements). In the following synthesis ofclozapine, Step 1 is an Ullmann coupling, a type of nucleophilic aromatic substitu-tion that uses a copper catalyst.МеOHOHNO2NO,UllmanncouplingHCl-CIH,N-N.(1)(2)2,5-Dichloro-2-Aminobenzoic acid(A)nitrobenzene(Anthranilic acid)MeMeMeNO,NH,AISO,HCl-N·H.Cl-(3)H.(4)H.(B)(C)Clozapine

Answered: A newer generation of antipsychotics,…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Show how you might bring about formation of the amide in Step 2.

A newer generation of antipsychotics, among them clozapine, are now used to treat
the symptoms of schizophrenia. These drugs are more effective than earlier drugs
in improving patient response in the areas of social withdrawal, apathy, memory,
comprehension, and judgment. They also produce fewer side effects such as seizures
and tardive dyskinesia (involuntary body movements). In the following synthesis of
clozapine, Step 1 is an Ullmann coupling, a type of nucleophilic aromatic substitu-
tion that uses a copper catalyst.
Ме
OH
OH
NO2
NO,
Ullmann
coupling
H
Cl-
CI
H,N-
N.
(1)
(2)
2,5-Dichloro-
2-Aminobenzoic acid
(A)
nitrobenzene
(Anthranilic acid)
Me
Me
Me
NO,
NH,
AISO,H
Cl-
N·
H.
Cl-
(3)
H.
(4)
H.
(B)
(C)
Clozapine

Expert Solution

Step 1

The reaction of acid and an amine results in the formation of amide. The amide is formed as a result of the attack of the lone pair present over nitrogen atom in the amine over the carbonyl centre. In other words, this reaction can be defined as a typical example of acid-base reaction or neutralization reaction.

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