MeshPL
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Amide N-alkylation?
Can amides be N-alkylated? If not, why?
If yes, would the following chain of reactions make any sense?
Benzoyl chloride -ammonia-> Benzamide -2*ethyl chloride/ethyl sulphate-> Diethylbenzamide -LiAlH4-> Benzyldiethylamine
Not that I have required aparature or reagents.
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CuReUS
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Amides can be N-alkylated,but its not easy.IIRC a Boron reagent is needed.
but this paper is interesting
http://www.mdpi.net/molecules/papers/41100333.pdf
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Crowfjord
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That paper does look interesting. Might make for a more amateur-friendly approach to amide alkylation. I've never heard of a boron reagent for that
sort of thing. Normally a very strong base like sodium hydride or sodamide is used.
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PHILOU Zrealone
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N alkylation can be done with formaldehyde...
Depending on reaction condition and réactants ratio...
R-CO-NH2 + CH2=O --> R-CO-NH-CH2OH <==> R-CO-N=CH2 + H2O
R-CO-NH2 + 2 CH2=O --> R-CO-N(-CH2OH)2
2 R-CO-NH2 + CH2=O --> R-CO-NH-CH2-NH-CO-R
PH Z (PHILOU Zrealone)
"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
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CuReUS
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see pg 39 of this books(sadly pg 37-38 cannot be viewed)
https://books.google.co.in/books?id=wPa-s7FgmZ8C&pg=PA84...
| Quote: | | I've never heard of a boron reagent for that sort of thing |
I saw it a few months back so I might have forgotten,I think I saw this(first reaction under "recent literature")
S. A. Rossi, K. W. Shimkin, Q. Xu, L. M. Mori-Quiroz, D. A. Watson, Org. Lett., 2013, 15, 2314-2317.
http://www.organic-chemistry.org/synthesis/C1N/amides2.shtm
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