a) Compound 1 is a nonsteroidal anti-inflammatory (NSAID) drug. Knowing that its thiazole ring can be synthesised using Hantzsch's method, propose the structure of the thioamide (2) and g-haloketone (3) fragments that take part in the reaction : CI COOH 1 2 3 b) Explain the reason why in the Hantzsch's synthesis of thiazoles the sulfur atom of the thioamide moiety prefers to attack the carbon-halogen bond while the nitrogen atom attacks the carbonyl group and not the other way around.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter23: Amines
Section: Chapter Questions
Problem 23.58P
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Solve bith parts a and b with detailed expalantion 

a) Compound 1 is a nonsteroidal anti-inflammatory (NSAID) drug. Knowing that
its thiazole ring can be synthesised using Hantzsch's method, propose the
structure of the thioamide (2) and g-haloketone (3) fragments that take part in
the reaction :
CI
COOH
1
2
3
b) Explain the reason why in the Hantzsch's synthesis of thiazoles the sulfur atom
of the thioamide moiety prefers to attack the carbon-halogen bond while the
nitrogen atom attacks the carbonyl group and not the other way around.
Transcribed Image Text:a) Compound 1 is a nonsteroidal anti-inflammatory (NSAID) drug. Knowing that its thiazole ring can be synthesised using Hantzsch's method, propose the structure of the thioamide (2) and g-haloketone (3) fragments that take part in the reaction : CI COOH 1 2 3 b) Explain the reason why in the Hantzsch's synthesis of thiazoles the sulfur atom of the thioamide moiety prefers to attack the carbon-halogen bond while the nitrogen atom attacks the carbonyl group and not the other way around.
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