RareEarth
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Will DCM react with amines?
Alkyl Halides normally react with amines but DCM is a bit more stable than most Alkyl Halides. The reason I ask is that I hope to use DCM as a bridge
to link some amines together.
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PHILOU Zrealone
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Hint...
DCM is a disguised form of formol and formaldehyde...
CH2Cl2
CH2(OH)2 --> CH2=O + H2O
PH Z (PHILOU Zrealone)
"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
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RareEarth
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What? I have no idea what you are trying to say.
My question is not whether or not it is capable of reacting. I know alkyl halides react with amines... My question was whether or not it will react,
ideally under non-forcing conditions. Some compounds are just so resonantly stabilized that they don't react like other members of their class.
I had a thought, I could perhaps throw some iodide salt into the mix to form insitu diiodomethane, which would certainly react.
[Edited on 11-8-2015 by RareEarth]
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BromicAcid
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Here is what I can tell you, I have seen plenty of solutions of amines made up in dichloromethane. I have seen this exclusively at the small scale, I
have had warnings handed down not to do this on scaleup due to incidents in the company. So the answer to your question would be yes, they can react,
but weather or not the reaction will be fast or not depends on the substrate and reaction conditions. Here are a few quick blurbs found on google in
about 3 minutes time:
http://www.tandfonline.com/doi/abs/10.1080/00304948409356172...
http://pipeline.corante.com/archives/2010/05/19/pyridines_an...
https://en.wikipedia.org/wiki/Menshutkin_reaction
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PHILOU Zrealone
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Quote: Originally posted by RareEarth  | What? I have no idea what you are trying to say.
My question is not whether or not it is capable of reacting. I know alkyl halides react with amines... My question was whether or not it will react,
ideally under non-forcing conditions. Some compounds are just so resonantly stabilized that they don't react like other members of their class.
I had a thought, I could perhaps throw some iodide salt into the mix to form insitu diiodomethane, which would certainly react.
[Edited on 11-8-2015 by RareEarth] |
If you leave DCM and amine enough time in contact they will react as if DCM was formaldehyde...
CH2Cl2 + H2O -amine base-> CH2(OH)2 + aminium chloride --> formimide related to the original amine.
So NH3 and CH2Cl2 will react if enough time and in a closed system to yield CH2=NH, hexamethylenetetramine and NH4Cl.
CH2=O + CH3-NH2 --> CH3-NH-CH2-NH-CH3 + CH3-N=CH2 + polymers like (-CH2-N(CH3)-)n + H2O
True that DIM will be more reactive than DBM itself more than DCM... so Finkelstein's will help but not with aceton solvent what would react with the
amine (Schiff's base formation).
[Edited on 12-8-2015 by PHILOU Zrealone]
PH Z (PHILOU Zrealone)
"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
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