Discovery of the antibiotic sulphanilamide led to rapid development of a large number of structurally related sulphonamides. Some of these were useful leads to compounds with other medicinal properties. Amongst these, sulfasalazine was active in the treatment of ulcerative colitis, a potentially fatal disease of the colon. As a medicinal chemist, you are about to carry out the synthesis of sulfasalazine, starting from aniline. Give the chemical names and draw the chemical structures of the reagents you will need to use for the all the steps marked (a)-(d). Aniline HO₂C HO (a) NIN- A CHN- Ac represents CH3CO Sulfasalazine S0,C1 SO,NH (b) (d) H₂N- SO,NH N (c) N pomol SO,NH Step (a) in question 5 above results in the para product only. Explain why this occurs.
Discovery of the antibiotic sulphanilamide led to rapid development of a large number of structurally related sulphonamides. Some of these were useful leads to compounds with other medicinal properties. Amongst these, sulfasalazine was active in the treatment of ulcerative colitis, a potentially fatal disease of the colon. As a medicinal chemist, you are about to carry out the synthesis of sulfasalazine, starting from aniline. Give the chemical names and draw the chemical structures of the reagents you will need to use for the all the steps marked (a)-(d). Aniline HO₂C HO (a) NIN- A CHN- Ac represents CH3CO Sulfasalazine S0,C1 SO,NH (b) (d) H₂N- SO,NH N (c) N pomol SO,NH Step (a) in question 5 above results in the para product only. Explain why this occurs.
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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![Discovery of the antibiotic sulphanilamide led to rapid development of a large
number of structurally related sulphonamides. Some of these were useful leads to
compounds with other medicinal properties. Amongst these, sulfasalazine was active
in the treatment of ulcerative colitis, a potentially fatal disease of the colon.
As a medicinal chemist, you are about to carry out the synthesis of sulfasalazine,
starting from aniline. Give the chemical names and draw the chemical structures of
the reagents you will need to use for the all the steps marked (a)-(d).
Aniline
HO₂C
HO
(a)
N=N-
ACHN
Ac represents CH3CO
Sulfasalazine
SO,NH
S0,C1
N
(b)
(d)
H₂N-
SO,NH
(c)
N
[Oro]
SO,NH
N
Step (a) in question 5 above results in the para product only. Explain why this
occurs.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fb02a1a1b-0e78-4aa5-b4cd-cc657e4d76cb%2F7920ed62-e9d5-434f-8b7c-511cc5a9b1e0%2Fs8hb8h_processed.png&w=3840&q=75)
Transcribed Image Text:Discovery of the antibiotic sulphanilamide led to rapid development of a large
number of structurally related sulphonamides. Some of these were useful leads to
compounds with other medicinal properties. Amongst these, sulfasalazine was active
in the treatment of ulcerative colitis, a potentially fatal disease of the colon.
As a medicinal chemist, you are about to carry out the synthesis of sulfasalazine,
starting from aniline. Give the chemical names and draw the chemical structures of
the reagents you will need to use for the all the steps marked (a)-(d).
Aniline
HO₂C
HO
(a)
N=N-
ACHN
Ac represents CH3CO
Sulfasalazine
SO,NH
S0,C1
N
(b)
(d)
H₂N-
SO,NH
(c)
N
[Oro]
SO,NH
N
Step (a) in question 5 above results in the para product only. Explain why this
occurs.
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