Sematilide

<h2 id="synthesis">Synthesis</h2>

<p>Sematilide can be synthesized from <a href="/facts/Benzocaine/2xMLUQf0">benzocaine</a> (1).<a class="footnote-ref" id="fnref:1" href="#fn:1"><sup>1</sup></a><a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a>  Reaction with <a href="/facts/Mesyl_chloride/8qMTp4rg">mesyl chloride</a>,  followed by saponification and removal of the water from the reaction mixture, gives sodium 4-[(methylsulfonyl)amino]benzoate (2). Chlorination with <a href="/facts/Thionyl_chloride/nWwvNtvd">thionyl chloride</a> gives 4-[(methylsulfonyl)amino]benzoyl chloride. Amide formation with <i>N</i>,<i>N</i>-diethylethylenediamine (3) then concludes the synthesis of sematilide (4).
</p>

<h2 id="references">References</h2>

<ol>
<li id="fn:1"><p>Lumma, William C.; Wohl, Ronald A.; Davey, David D.; Argentieri, Thomas M.; Devita, Robert J.; Gomez, Robert P.; Jain, Vijay K.; Marisca, Anthony J.; Morgan, Thomas K.; Reiser, H. J. (1987). "Rational design of 4-[(methylsulfonyl)amino]benzamides as class III antiarrhythmic agents". Journal of Medicinal Chemistry. 30 (5): 755–758. doi:10.1021/jm00388a001. PMID 3572962. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li>
<li id="fn:2"><p>David D. Davey, William C. Lumma, Jr., Ronald A. Wohl, U.S. patent 4,544,654 (1985 to Schering A.G.) <a href="https://patents.google.com/patent/US4544654" target="_blank">https://patents.google.com/patent/US4544654</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li>
</ol>

Sematilide open-in-new

Sematilide