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Chapter 19: Q19P (page 1003)

Show how you would use the same sulfonyl chloride as used in the sulfanilamide synthesis to make sulfathiazole and sulfapyridine.

Short Answer

Expert verified

4-acetamidobenzenesulfonyl chloride on reaction with thiazol-2-amine undergoes nucleophilic attack of amino group onto the sulphur of sulfonyl chloride group as sulphur is electron deficient so acts as an electrophile and hydrogen chloride eliminates as leaving group. In next step, on treatment with hydrogen chloride and heat, acetanilide group gets reduced to amino group and formation of sulfathiazole occurs.

Formation of sulfathiazole

Step by step solution

01

Step-1. Formation of sulfathiazole:

4-acetamidobenzenesulfonyl chloride on reaction with thiazol-2-amine undergoes nucleophilic attack of amino group onto the sulphur of sulfonyl chloride group as sulphur is electron deficient so acts as an electrophile and hydrogen chloride eliminates as leaving group. In next step, on treatment with hydrogen chloride and heat, acetanilide group gets reduced to amino group and formation of sulfathiazole occurs.

Formation of sulfathiazole

02

Step-2. Formation of sulfapyridine:

4-acetamidobenzenesulfonyl chloride on reaction with pyridine-2-amine undergoes nucleophilic attack of amino group onto the sulphur of sulfonyl chloride group as sulphur is electron deficient so acts as an electrophile and hydrogen chloride eliminates as leaving group. In next step, on treatment with hydrogen chloride and heat, acetanilide group gets reduced to amino group and formation of sulfapyridine occurs.

Formation of sulfapyridine

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Most popular questions from this chapter

Macrolide antibiotics all have large rings (macrocycle) in which an ester makes the ring; a cyclic ester is termed a lactone. One example is erythromycin A, first isolated from soil bacteria in the 1950鈥檚. Over time, some pathogenic bacteria have developed resistance to erythromycin by evolving an enzymatic mechanism to cleave the macrocycle at the ketone. To counter this resistance, chemists modified the erythromycin structure to replace the ketone with an amine that the bacteria could not detoxify. This modified antibiotic, azithromycin, trade name Zithromax庐, is one of the most prescribed drugs in the world for respiratory infections.

(a) Identify the lactone group in each structure that merits the classification as macrolides.

(b) Two groups are circled. What type of functional group are they? Explain

(c) Identify the ketone in erythromycin targeted by bacteria as the site for detoxification.

(d) Identify the amine in azithromycin. What type of amine is it?

(e) From what you know about the reactivity of ketones and amines, why was an amine a good choice to be the 鈥渃hemical opposite of a ketone鈥�?

Give the products expected from the following reactions:

(a) acetyl chloride + ethylamine

(b) benzoyl chloride +dimethylamine

(c) hexanoyl chloride + piperidine

Propose a mechanism for nitration of pyridine at the 4-position, and show why this orientation is not observed.

Show how you would accomplish the following synthetic conversions.

(a) benzyl bromide to benzylamine

(b) 1-bromo-2-phenylethane to 3-phenylpropan-1-amine

(c) pentanoic acid to pentan-1-amine

(d) pentanoic acid to hexan-1-amine

(e) (R)-2-bromobutane to (S)-butan-2-amine

(f) (R)-2-bromobutane to (S)-2-methylbutan-1-amine

(g) hexan-2-one to 1-amino-2-methylhexan-2-ol

(a) Show how fragmentation occurs to give the base peak at m/z 58 in the mass spectrum of ethyl propyl amine (N-ethylpropan-1-amine), shown below.

(b) Show how a similar cleavage in the ethyl group gives an ion of m/z72.

(c) Explain why the peak at m/z 72 is much weaker than the one at m/z 58.
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