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 UC235 - 15-1-2020 at 17:24
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?vannylaholic - 16-1-2020 at 08:37
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 vannylaholic - 16-1-2020 at 08:49
Also this is the exact mechanism that urea/formaldehyde resin is formed I'm just modifying the mol ratios and reaction conditions
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 luckyarkoma - 27-1-2021 at 21:37
*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]vannylaholic - 29-1-2021 at 12:30
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 , clearly_not_atara - 29-1-2021 at 13:06
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 karlos³ - 29-1-2021 at 20:02
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]arkoma - 30-1-2021 at 01:15
fuck, that makes me the newbee at not quite seven......
