morsagh
Hazard to Others
Posts: 187
Registered: 20-2-2014
Member Is Offline
Mood: No Mood
|
|
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?
|
|
|
aga
Forum Drunkard
Posts: 7030
Registered: 25-3-2014
Member Is Offline
|
|
.
|
|
|
Crowfjord
Hazard to Others
Posts: 390
Registered: 20-1-2013
Location: Pacific Northwest
Member Is Offline
Mood: Ever so slowly crystallizing...
|
|
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]
|
|
|
zed
International Hazard
Posts: 2284
Registered: 6-9-2008
Location: Great State of Jefferson, City of Portland
Member Is Offline
Mood: Semi-repentant Sith Lord
|
|
Amides can be alkylated by Alcohols, at elevated pressures and temperature. Somewhere, via the search engine, there are many discussions of such
matters.
|
|
|
Nicodem
|
Thread Moved
22-6-2016 at 13:15 |
![[*]](images/xpblue/default_icon.gif){kind=icon}
