You can see that it is an azo dye, can't you? Knowing that an azo compound is produced for the coupling of a diazonium ion with a strongly activated aromatic compound, can you suggest the starting materials for the preparation of Protonsil? And from here, I'm sure you can make an educated guess on what the structure of sulfanilamide is.

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
Chapter31: Immunochemistry
Section: Chapter Questions
Problem 31.72P
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Read the passage first then please answer in full details:
In 1935, the daughter of Gerhard Domagk, a doctor at I. G. Farbenindustrie, a
German dye manufacturing company, contracted a streptococcal infection from a
pin prick. As his daughter was nearly dying, Domagk took the risk of giving her
an oral dose of a dye called Protonsil. This dye had been shown to inhibit the
growth of streptococci in mice. Very soon the little girl recovered. Domagk's
gamble not only saved his daughter's life, but it also sparked a new and
impressively productive phase in modern chemotherapy.
The following year, in 1936, Ernest Fourneau of the Pasteur Institute in Paris
demonstrated that Protonsi! breaks down in the human body to produce
sulfan:lamide. He also demonstrated that sulfanilamide is the active agent against
streptococci. Fourneau's announcement of this result started the search for other
chemicals related to sulfanilamide that might have even better chemotherapeutic
effects. Thousands of chemical variations were played on the sulfanilamide
theme: the structure of sulfanilamide was varied in almost every imaginable way.
Now, after that long story, here's the problem that you're supposed to work on.
The structure of Protonsil is given below.
NH2
H2N-
N= N-
NH2
Protonsil
Transcribed Image Text:In 1935, the daughter of Gerhard Domagk, a doctor at I. G. Farbenindustrie, a German dye manufacturing company, contracted a streptococcal infection from a pin prick. As his daughter was nearly dying, Domagk took the risk of giving her an oral dose of a dye called Protonsil. This dye had been shown to inhibit the growth of streptococci in mice. Very soon the little girl recovered. Domagk's gamble not only saved his daughter's life, but it also sparked a new and impressively productive phase in modern chemotherapy. The following year, in 1936, Ernest Fourneau of the Pasteur Institute in Paris demonstrated that Protonsi! breaks down in the human body to produce sulfan:lamide. He also demonstrated that sulfanilamide is the active agent against streptococci. Fourneau's announcement of this result started the search for other chemicals related to sulfanilamide that might have even better chemotherapeutic effects. Thousands of chemical variations were played on the sulfanilamide theme: the structure of sulfanilamide was varied in almost every imaginable way. Now, after that long story, here's the problem that you're supposed to work on. The structure of Protonsil is given below. NH2 H2N- N= N- NH2 Protonsil
You can see that it is an azo dye, can't you? Knowing that an azo compound
is produced for the coupling of a diazonium ion with a strongly activated
aromatic compound, can you suggest the starting materials for the
preparation of Protonsil? And from here, I'm sure you can make an
educated guess on what the structure of sulfanilamide is.
Transcribed Image Text:You can see that it is an azo dye, can't you? Knowing that an azo compound is produced for the coupling of a diazonium ion with a strongly activated aromatic compound, can you suggest the starting materials for the preparation of Protonsil? And from here, I'm sure you can make an educated guess on what the structure of sulfanilamide is.
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