morsagh
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Alkylation of amides
Why aren't amides used for synthesis of secondary amines by alkylation of amide with alkyl halide? Where is problem in this synthesis?
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aga
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Crowfjord
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Amides are poor nucleophiles due to the nitrogen's lone pair of electrons being tied up in resonance with the carbonyl. They can be alkylated (I
think), if they are first deprotonated with a strong base like lithium diisopropylamide (LDA). Imides can also similarly be alkylated after forming
the salt.
Saccharine, an amide/sulfonamide, can also be N-alkylated to synthesize amines. See the thread here.
[Edited on 21-6-2016 by Crowfjord]
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zed
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Amides can be alkylated by Alcohols, at elevated pressures and temperature. Somewhere, via the search engine, there are many discussions of such
matters.
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Nicodem
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Thread Moved
22-6-2016 at 13:15 |
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