Cl CI CI CI CISO,H (1) NH3 Cl (2) СООН СООН 2,4-Dichlorobenzoic acid H,N. heat H. Cl Cl Furfurylamine H,N. H,N. COOH СООН Furosemide

Fundamentals Of Analytical Chemistry
9th Edition
ISBN:9781285640686
Author:Skoog
Publisher:Skoog
Chapter9: Aqueous Solutions And Chemical Equilibria
Section: Chapter Questions
Problem 9.20QAP
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A diuretic is a compound that causes increased urination and thereby reduces fluid volume in the body. An important use of diuretics in clinical medicine is in the reduction of the fluid buildup, particularly in the lungs, that is associated with congestive heart failure. It is also used as an antihypertensive (i.e., to reduce blood pressure). Furosemide, an exceptionally potent diuretic, is prescribed under 30 or more trade names, the best known of which is Lasix. The synthesis of furosemide begins with treatment of 2,4-dichlorobenzoic acid with chlorosulfonic acid in a reaction called chlorosulfonation. The product of this reaction is then treated with ammonia followed by heating with furfurylamine.

Q. Is furosemide chiral? If so, which of the possible stereoisomers are formed in this synthesis?

Cl
CI
CI
CI
CISO,H
(1)
NH3
Cl
(2)
СООН
СООН
2,4-Dichlorobenzoic acid
H,N.
heat
H.
Cl
Cl
Furfurylamine
H,N.
H,N.
COOH
СООН
Furosemide
Transcribed Image Text:Cl CI CI CI CISO,H (1) NH3 Cl (2) СООН СООН 2,4-Dichlorobenzoic acid H,N. heat H. Cl Cl Furfurylamine H,N. H,N. COOH СООН Furosemide
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