Discovery of the antibiotic sulphanilamide led to rapid development of a large number of structurally related sulphonamides. Some of these were useful leads to compounds with other medicinal properties. Amongst these, sulfasalazine was active in the treatment of ulcerative colitis, a potentially fatal disease of the colon. As a medicinal chemist, you are about to carry out the synthesis of sulfasalazine, starting from aniline. Give the chemical names and draw the chemical structures of the reagents you will need to use for the all the steps marked (a)-(d). Aniline HO₂C HO (a) NIN- A CHN- Ac represents CH3CO Sulfasalazine S0,C1 SO,NH (b) (d) H₂N- SO,NH N (c) N pomol SO,NH Step (a) in question 5 above results in the para product only. Explain why this occurs.

Discovery of the antibiotic sulphanilamide led to rapid development of a large number of structurally related sulphonamides. Some of these were useful leads to compounds with other medicinal properties. Amongst these, sulfasalazine was active in the treatment of ulcerative colitis, a potentially fatal disease of the colon. As a medicinal chemist, you are about to carry out the synthesis of sulfasalazine, starting from aniline. Give the chemical names and draw the chemical structures of the reagents you will need to use for the all the steps marked (a)-(d). Aniline HO₂C HO (a) NIN- A CHN- Ac represents CH3CO Sulfasalazine S0,C1 SO,NH (b) (d) H₂N- SO,NH N (c) N pomol SO,NH Step (a) in question 5 above results in the para product only. Explain why this occurs.

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

Chapter18: Functional Derivatives Of Carboxylic Acids

Section: Chapter Questions

Problem 18.42P

See similar textbooks

Similar questions

Several sulfonylureas, a class of compounds containing RSO2NHCONHR, are useful drugs as orally active replacements for injected insulin in patients with adult-onset diabetes. These drugs decrease blood glucose concentrations by stimulating b cells of the pancreas to release insulin and by increasing the sensitivity of insulin receptors in peripheral tissues to insulin stimulation. Tolbutamide is synthesized by the reaction of the sodium salt of p-toluenesulfonamide and ethyl N-butylcarbamate . Propose a mechanism for this step.
Show how to synthesize the following amines from the indicated starting materials byacylation–reduction.(a) N-butylpiperidine from piperidine
The 1H- and 13C-NMR data of an ester of molecular formula C6H10O2 are given below. Also shown are the COSY and HETCOR NMR spectra of the ester. Draw the structure of the ester, explaining how you reach your conclusion. 1H-NMR: 7.20-6.90 (1H), 5.85 (1H), 4.16 (2H), 1.88 (3H), 1.31 (3H) ppm 13C-NMR: 166.7, 144.5, 123.0 , 60.2, 18.0, 14.3 ppm
Atenolol is a beta blocker medication primarily used to treat high blood pressure and heart- associated chest pain. Other uses include the prevention of migraines and treatment of certain irregular heart beats It is taken by mouth or by injection into a vein. It can also be used with other blood pressure medications. OH .N. CH3 ČH3 H2N° suggest industrial synthetic approach towards synthesis of this drug (atenolol) and provide reasons and advantages of your proposed synthetic approach.
An amine of unknown structure contains one nitrogen and nine carbon atoms. The 13C-NMR spectrum shows only five signals, all between 20 and 60 ppm. Three cycles of Hofmann elimination sequence [(1) CH3I; (2) Ag2O, H3O; (3) heat] give trimethylamine and 1,4,8-nonatriene. Propose a structural formula for the amine.
During a recent synthesis of hispidospermidin, a fungal isolate and an inhibitor of phospholipase C, the investigators employed employed a novel Friedel-Crafts acylation on a nonaromatic system (J. Am. Chem. Soc. 1998, 120, 4039-4040). The following acid chloride was treated with a Lewis acid, affording a mixture of two products, 1 and 2. Propose a plausible mechanism for the formation of compounds 1 and 2. CI AICI 进一步农 COCI 2 Part 1 Incorrect. Which of the four mechanistic steps is happening? Add curved arrow(s) to draw the first step of the mechanism. Modify the given drawing of the products as needed to show the intermediate that is formed in this step. Use the +/- tools to add/remove charges. CH₂ H St Edit Drawing H₂C H CH₂ CI Q M ΟΣ
In an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?
Show how to synthesize the following amines from the indicated starting materials.(a) N-cyclopentylaniline from aniline
Show how to synthesize the following amines from the indicated starting materials.(a) N-cyclopentylaniline from aniline (b) N-ethylpyrrolidine from pyrrolidine
Acid-catalyzed hydrolysis of HOCH2CH2C(CH3)2CN forms compound A (C6H10O2). A shows a strong peak in its IR spectrum at 1770 cm-1 and the following signals in its 1H NMR spectrum: 1.27 (singlet, 6 H), 2.12 (triplet, 2 H), and 4.26 (triplet, 2 H) ppm. Draw the structure for A and give a stepwise mechanism that accounts for its formation.
(D)The best route to synthesise aromatic primary amines is by reduction of the corresponding nitro compounds. Draw the reaction scheme for the preparation of p-toluidine.
In the mid-1930s a substance was isolated from a fungus that is a parasite of ryes and other grasses. This alkaloid, lysergic acid, has been of great interest to chemists because of its strange, dramatic action on the human mind. Many derivatives of lysergic acid are known, some with medicinal applications. Perhaps the best known derivative of lysergic acid is the potent hallucinogen lysergic acid diethylamide (LSD): మగవా జి N-H LSD (CH25N;O) Like other alkaloids, LSD is a weak base, with Kp = 7.6 × 107. What is the pH of a 0.94 M solution of LSD? pH =