vannylaholic
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primary amines using urea and aldehydes or ketones ?
i will be reacting a 1:1 mol ratio of acetone and urea in anhydrous methanol , with a ga/al alloy as a reducing agent , has anyone seen any literature
pertaining to the alkylation of urea followed by hydrolysis to to afford the alkyl amine , ive searched up and down for a source but i cant find one
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UC235
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Urea will not form any sort of imine that can be reduced since it is an amide, not an amine. Where did you get this idea?
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vannylaholic
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There are multiple sources that use urea in a condensation reaction with diethyl malonate thats where the idea came from . I've also read litature
where urea itsself is hydrogenated to form 2 nh3 and formaldehyde which condenses to form ammonia gas and methylimine which can be reduced to the
primairy amine , all I'm proposing is that the liberated ammonia is reacted in situ with acetone and further reduced to the amine
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vannylaholic
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Also this is the exact mechanism that urea/formaldehyde resin is formed I'm just modifying the mol ratios and reaction conditions
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vannylaholic
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Source
Quote: Originally posted by UC235  | | Urea will not form any sort of imine that can be reduced since it is an amide, not an amine. Where did you get this idea? |
https://www.organic-chemistry.org/abstracts/lit2/126.shtm I finally found a source . Only a first calls for the formation of the carbonate
followed by reductive amination and hydrolysis. And I just came up with the idea of brainstorming some time ago , I come up with lots of random ideas
every day, and if there is no literature easily accessible about them, I research them and attempt them to see if they are feasible I don't know why
I'm just difficult I guess. I am not a classically educated organic chemist but I am relatively intelligent and comprehend the art of chemistry, plus
this is literally been my hobby from the age of 10. It seems that people on this forum think I'm a hoodlum looking for handouts but all I'm looking
for is honest conversation about these reactions to better my grasp an organic chemistry and biochemistry. And maybe someday contribute a little bit
to the science, if I'm lucky
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arkoma
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The paper ref'd above:
Attachment: reductive alkylation urea.pdf (83kB)
This file has been downloaded 282 times
*edit* Hoodlum?!? So what if ya are? My best friends are all hoodlums. Don't let the occasional asshole here get ya down, Vannylaholic.
*edit* spelling
[Edited on 1-28-2021 by arkoma]
[Edited on 1-28-2021 by arkoma]
"We believe the knowledge and cultural heritage of mankind should be accessible to all people around the world, regardless of their wealth, social
status, nationality, citizenship, etc" z-lib
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vannylaholic
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Thanks arkoma . That's a little bit of a morale boost I've been part of this form for a while And haven't got a real positive reaction yet . also
thanks for the ref ,
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clearly_not_atara
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The condensation of urea and malonic acid generally takes place at high temperatures -- too high for acetone at standard pressure. Additionally, the
tetrahedral intermediate is quite unstable and rapidly eliminates alcohol, whereas no such stabilizing elimination is possible for the urea+acetone
TI. When using formaldehyde, the tetrahedral intermediate has less steric instability.
Therefore, I do not think a stable condensation product can be obtained from urea and acetone by alkylimino-deoxo bisubstitution. You might cause some
other reaction, though.
| Quote: | | I've been part of this form for a while |
Not eight years, though 
[Edited on 04-20-1969 by clearly_not_atara]
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karlos³
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atara you old braggart 
Edit: what the hell, I'm here since the tenth january ten years ago! I thought the registration date was displayed anglo style and my anniversary is
on the first october 
I missed own tenth anniversary here, oh no!
[Edited on 30-1-2021 by karlos³]
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arkoma
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fuck, that makes me the newbee at not quite seven......
*edit*spelling
[Edited on 1-30-2021 by arkoma]
"We believe the knowledge and cultural heritage of mankind should be accessible to all people around the world, regardless of their wealth, social
status, nationality, citizenship, etc" z-lib
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