Ozonelabs
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Ozonelabs synthesis of N-Phenylmaleimide
This is a synthesis of N-Phenylmaleimide yielding exquisite canary yellow crystals.
We would appreciate any feedback or improvements on the synthesis that you many have.
Thank you,
P.S. Luminol pdf coming soon
Attachment: N-Phenylmaleimide.pdf (441kB)
This file has been downloaded 4010 times
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panziandi
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Nice prep and photo! I recall some interest in ring substituted phenylmaleimides or succinamides being researched at Oxford University as (I may be
wrong here) enzyme inhibitors/drugs but can not remember what the targets were 
perhaps a lit search will yield some clues as to what I'm thinking about.
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Klute
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Very nice! I like the pdf presentation! This could actually go into prepublication...
I would love to hear of the use of this product as a dienophile.
Nothing much to add! Good work!
Love to see more documents/work like this!
\"You can battle with a demon, you can embrace a demon; what the hell can you do with a fucking spiritual computer?\"
-Alice Parr
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Nicodem
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Nice report.
I would however suggest to also try a direct one-step preparation which is also possible by simply refluxing maleic anhydride, aniline, TsOH (or other
suitable acid catalyst) in toluene or xylene in the presence of a polymerisation inhibitor such as hydroquinone or similar (most members here have
troubles obtaining acetanhydride). One such example is described in patent EP726252 (there are many other examples in the patent literature, but this
is I believe the simplest).
Panziandi, I doubt any N-phenylmaleimides could be seriously considered as (reversible) enzyme inhibitors or potential drugs. They have one of those
type of chemical functionalities that are consider a NO in medicinal chemistry - the maleimide group is a strongly electrophilic, it is Michael
alkylator, a dienophile and an enophile...
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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panziandi
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No no, this was about 6 years ago when I was in the pharmacology department someone over in chemistry was making these derivatives (I thought it was
to do with trying to inhibit some enzyme perhaps it wasn't but the work was related to something inthe pharmacology department!), perhaps purely for
research but it definitely was based on either the succinimides or maleimides (most likely the succinimide). I remember that they used the two step
process whereby they brought about the cyclic imide by refluxing with acetic anhydride as described by Ozone. I will try and do a literature search
because they must have published something!
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Ozonelabs
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N-Phenylmaleimide Anthracene Adduct PDF
Diels-Alder with N-Phenylmaleimide and Anthracene.
As requested in our last thread.
Attachment: NPMAAdduct.pdf (286kB)
This file has been downloaded 705 times
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Klute
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Beautifull! Thank you very much!
So what's next on your list? Any uses of the formed product?
\"You can battle with a demon, you can embrace a demon; what the hell can you do with a fucking spiritual computer?\"
-Alice Parr
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Ozonelabs
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Klute- we have been thinking very hard about what to do next and have been drawing blanks...
We were considering a Luminol synthesis (out of academic interest and becuase we were asked for one via e-mail), perhaps showing a Vilsmeier Haack
formylation, reductions etc.
This is why we ask for peoples requests! Otherwise we are unsure as to what people would like to see...
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Formula409
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| Quote: | Originally posted by Ozonelabs
This is why we ask for peoples requests! Otherwise we are unsure as to what people would like to see... |
Luminol sounds interesting. What route would you be taking? Keep up the great work.
Formula409.
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Ozonelabs
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Formula409-
Phthalic Anhydride to 3/4 Nitrophthallic Anhydride with Fuming HNO3 and conc HNO3/ H2SO4.
3-Nitrophthalic Anhydride to 5-nitro-2,3-dihydro-1,4-phthalazinedione via sodium salt of the former and either Hydrazinium
Sulphate or Hydrazine Hydrate.
5-nitro-2,3-dihydro-1,4-phthalazinedione to luminol via sodium hydrosulfite.
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bfesser
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Ozonelabs, did you take the melting range of your anthracene adduct? Thanks.
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Paddywhacker
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You've drawn fumaranilic acid as the intermediate.
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Drunkguy
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Anybody got any idea what the motivations might be for making this product?
It's elegant chemistry, although what function (if any) does N-Phenylmaleimide actually serve?
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