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

Chemistry
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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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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. Propose a mechanism for the chlorosulfonation reaction in Step (1).

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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