Me Me Me Cl CI CI (A) (В) Diazepam Cl- Me CI 4-Chloro-N-methylaniline Benzoyl chloride

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter19: Carboxylic Anhydrides, Esters, And Amides
Section: Chapter Questions
Problem 19.43P
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Diazepam, better known as Valium, is a central nervous system (CNS) sedative/ hypnotic. As a sedative, it diminishes activity and excitement and thereby has a calming effect. Back in 1976, based on the number of new and refilled prescriptions processed,
diazepam was the most prescribed drug in the United States. Following is a retrosynthetic analysis for a synthesis of diazepam. Note that the formation of compound B involves a Friedel-Crafts acylation. In this reaction, it is necessary to protect the 2° amine by prior treatment with acetic anhydride. The acetyl-protecting group is then removed by treatment with aqueous NaOH followed by careful acidification with HCl.

Q.Given this retrosynthetic analysis, propose a synthesis for diazepam

Me
Me
Me
Cl
CI
CI
(A)
(В)
Diazepam
Cl-
Me
CI
4-Chloro-N-methylaniline
Benzoyl chloride
Transcribed Image Text:Me Me Me Cl CI CI (A) (В) Diazepam Cl- Me CI 4-Chloro-N-methylaniline Benzoyl chloride
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