DionSukhram6
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Amide Reaction with Benzene Derivative?
So I've been trying to come up with a process to make Marfey's Reagent from simple chemicals but I'm stuck on the last few steps. I would react
L-alanine with ammonium Carbonate then dehydrate it but the product of this is neutral, while a search for L-alanine amide says that it should be
positively charged and have one more hydrogen than what I see from my reaction. Then, I would react this with 1-fluoro-2,4-dinitrobenzene and, as far
as I know, it should be able to substitute with a hydrogen on the benzene ring, since it's positively charged, giving the desired product, but I
can't figure out what the other reaction product would be (maybe it's just because I haven't been doing organic Chem for very long)
Can somebody help clarify this please?
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Boffis
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The problem I can see is that the fluorine in a 2,4-dinitrofluorobenzene derivative will be fairly reactive so you my need to think about how
introduce the amino-amide group without reacting with the fluorine. You may need to start the other way round and introduce the nitro groups after you
have added the 2-aminopropanamide unit. Perhaps start with 3-fluoroaniline and react it with lactamide (2-hydroxypropanamide) or 2-chloropropanamide.
The latter can be prepared from methyl 2-chloropropanoate ester by controlled ammoniolysis.
I think you to check out the original synthesis. For this you will need to look at the original paper:
P. Marfey, Carlsberg Res. Commun., 49 (1984) 591.
This article is freely available online from the Springer website and described the synthesis in outlined from 1,5-difluoro-2,4-dinitrobenzene and the
appropriate amide. You will now have to find out how to prepare the individual components.
Attachment: Marfey 1984.pdf (373kB)
This file has been downloaded 364 times
[Edited on 17-9-2017 by Boffis]
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