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3) Write out à Synthetic route to procure the given Product. 415

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter27: Amines

Section: Chapter Questions

Problem 2E

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3) Write out à Synthetic route to procure the given
Product.
414

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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 Step (3).