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ErgoloidMesylate
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Will sodium and absolute ethanol reduce acetamide?
https://en.wikipedia.org/wiki/Bouveault%E2%80%93Blanc_reduct...
[Edited on 18-8-2022 by ErgoloidMesylate]
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Texium
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No
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ErgoloidMesylate
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Looks like heating acetamide with sodium borohydride makes acetonitrile, which can be reduced with sodium and alcohol to ethylamine
Edit
Heat at 150 c for 6 hours, evolves ammonia, makes alcohol, and acetonitrile in theory.
But that is ridiculous.
I think a better idea is just to reduce nitroethane and be done with it.
[Edited on 22-8-2022 by ErgoloidMesylate]
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clearly_not_atara
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There are less silly ways to dehydrate acetamide, like simply refluxing over alumina. And acetonitrile is useful enough that it can be worth it to
make/buy for its own sake. Polar, aprotic, low boiling. In fact buying acetonitrile is probably the easier option — it's much less of a pain to
purchase than nitroethane!
But the reduction is a shitshow. You have to make sodium in an inefficient thermochemical reaction or an elaborate electrochemical setup. Four moles
of sodium for one mole of EtNH2 theoretical, more in practice.
However, cobalt-on-nitrogen-doped-carbon catalysts can catalyze the efficient reduction of nitriles with hydrogen:
https://www.sciencedirect.com/science/article/pii/S187853522...
Unfortunately, the paper's interpretation of "mild" conditions refers to 7 bar hydrogen at 110 C. If this were a salsa, it would make children cry.
The Co@CNx catalysts can also be made from sucrose and melamine and can utilize formic acid as a reducing agent:
https://doi.org/10.1002/cssc.201802163
I am not aware of a nitrile reduction using Co@CNx with formic acid, but I also don't know that it doesn't work.
[Edited on 22-8-2022 by clearly_not_atara]
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ErgoloidMesylate
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Getting ready to publish a better book on the topic, having looked up an old method of concentrated ammonia dissolved in ethanol and adding ethyl
halide, I believe I have found the preferred method to accomplish this, which will be put in my new book coming out.
Anhydrous ammonia in anhydrous ethanol and adding ethyl halide. Boiling off the ethanol, and freebasing the amine salts to distill and separate and
dry.
Should do the trick nicely and be the way it is done even here on this site.
Cannula transfer and cannula filtering is used for lysergic synth Compressed air and remove co2
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clearly_not_atara
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http://archives.njit.edu/vol01/etd/1960s/1964/njit-etd1964-0...
According to this MS thesis from 1964, ethyl bromide reacts with urea at 100 C in DMF.
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ErgoloidMesylate
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The availability of DMF becomes a huge issue. Perhaps you can include it in your book.
My method involves easily obtainable items.
Cannula transfer and cannula filtering is used for lysergic synth Compressed air and remove co2
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clearly_not_atara
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Solvents are usually replaceable. DMSO would react with the substrate, but other polar solvents might do the trick.
The thesis mentions other rxn conditions as well, but mostly I thought the alkylation of urea was just really interesting.
Good luck writing the book, I hear that takes a while.
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Texium
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Thread Split
7-5-2023 at 09:34 |
SplendidAcylation
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I haven't read the whole thread so I apologise if I am repeating what others have said, but has the Delepine reaction been considered?
I noticed the Hofmann rearrangement and Gabriel synthesis were mentioned...
For the preparation of propionamide for the former, propionic acid + urea would work.
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ErgoloidMesylate
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Quote: Originally posted by ErgoloidMesylate  |
... having looked up an old method of concentrated ammonia dissolved in ethanol and adding ethyl halide, I believe I have found ...
Anhydrous ammonia in anhydrous ethanol and adding ethyl halide. Boiling off the ethanol, and freebasing the amine salts to distill and separate and
dry.
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May have to add hcl to ensure it is all converted to salt, before distilling off the ethanol.
[Edited on 7-5-2023 by ErgoloidMesylate]
Cannula transfer and cannula filtering is used for lysergic synth Compressed air and remove co2
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