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Author: Subject: Substituted quinazolines
amrhamed2
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[*] posted on 12-11-2008 at 08:10
Substituted quinazolines

In order to substitute the chlorine with different anilines the author used acidulated water or benzene

I don't have the paper so I don't know the details but from my experience I know that this ester is very reactive and can form amide with amines easily

I am just wondering .........does this reaction proceeds at rt or needs reflux (step 2) and how to avoid reaction between ester and amine if reflux was used

[Edited on 12-11-2008 by amrhamed2]

11-12-2008 6-04-21 PM.png - 10kB



amr h mahmoud
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amrhamed2
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[*] posted on 12-11-2008 at 08:12


Here is the abstract of the paper

Synthesis and antiinflammatory activity of ethyl 4-(anilino substituted)-2-quinazolinecarboxylates. Mekuskiene, Giedrute; Udrenaite, Emilija; Gaidelis, Povilas; Vainilavicius, Povilas. Faculty of Chemistry, Vilnius University, Vilnius, Lithuania. Chemija (1999), 10(3), 214-217. Publisher: Academia, CODEN: CHMJES ISSN: 0235-7216. Journal written in English. CAN 133:362749 AN 2000:675531 CAPLUS

Abstract

Treatment of Et 4-oxo-3,4-dihydro-2-quinazolinecarboxylate with thionyl chloride resulted in Et 4-chloro-3,4-dihydro-2-quinazolinecarboxylate formation. The latter reacted with arom. amines in acidified water or benzene to form Et 4-(anilino substituted)-2-quinazolinecarboxylate possessing antiinflammatory activity.



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[*] posted on 13-11-2008 at 05:51


Aminolysis of desactivated esters with aromatic amines requires very hot temperatures and oftene xcessive reaction times.
When adding SOCl2 to the substarte, youa re forming a chloro-iminium species, which is very reactive and will attack the amine long before the ester. So no worry on that side IMHO.



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