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Author Topic: SN on iodosafrole with methylamine - TEST !  (Read 649 times)

Quantum Dude

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Re: SN on iodosafrole with methylamine - TEST !
« Reply #20 on: August 16, 2010, 01:49:06 AM »
Quote from: jon on August 16, 2010, 01:44:14 AM
m.p. of the acetate was 100C because it was a hydrate.
or a hemihdrate.
i would like to also comment that the commonly used wacker oxidation gives rearrangemant products also.
Its true but the latter can be separated by fractional distillation of MDP2P. The major contaminant being isosafrole acording to TSII. Amino derivatives that wouldnt be properly separated in your protocol would be in the final product as hydrochlorides. Thats where I was getting at.

It would bee nice to have a mp for the hydrochloride jon but I do understand that many studies reports very different values so its hard to actually know. I myself always obtained a rather broad value from reductive amination.
« Last Edit: August 16, 2010, 01:54:01 AM by Quantum Dude »

jon

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Re: SN on iodosafrole with methylamine - TEST !
« Reply #21 on: August 16, 2010, 01:57:09 AM »
the o2 system gives aldehydes i think the benzoquinone is less prone to that.
could explain your broad values. another is that it was racemates too.
i guess the guys getting the mdp2p from china have the sharpest melting points so to speak as they use the peracid process very convenient for them.
« Last Edit: August 16, 2010, 02:05:04 AM by jon »

jon

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Re: SN on iodosafrole with methylamine - TEST !
« Reply #22 on: August 16, 2010, 01:58:55 AM »
i can say this it was pretty good shit.

headstrong

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Re: SN on iodosafrole with methylamine - TEST !
« Reply #23 on: August 18, 2010, 10:37:20 AM »
By simply doing HCl titrating to iPr-OH - MeNH2 solution we can determine how much MeNH2 out from naOH solution.
Another idea, start from HCl salt of MeNH2, and drop saturated KOH - iPr-OH (or MeOH?)  solution into that salt, by this way you can heat it to push MeNH2 flow into IPA without worry about water.

jon

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Re: SN on iodosafrole with methylamine - TEST !
« Reply #24 on: August 18, 2010, 10:54:48 AM »
if you want to spend a lot of time in the lab scratching your head and nuts, and cursing. ;D
drop saturated naoh onto methylamine hcl it's more controllable because you need to control the rate at which it bubbles in, too fast, and it bubbles out.
you need a suckback trap and a gas dispersion device at the end of the tubing to get good results.

-vanadium-

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Re: SN on iodosafrole with methylamine - TEST !
« Reply #25 on: August 18, 2010, 04:42:06 PM »
you can add Na to isopropanol, then neutralise it with methylamine HCl. Filter the NaCl and store it over sieve.

jon

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Re: SN on iodosafrole with methylamine - TEST !
« Reply #26 on: August 18, 2010, 04:46:07 PM »
or you can add triethylamine to it to neutralize it that's convenient too.

mrhawke

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Re: SN on iodosafrole with methylamine - TEST !
« Reply #27 on: April 10, 2011, 11:58:57 AM »
Dr.Methoxy:

You have an organic bromide. You want an organic iodide. So just get your bromo, dissolve it in acetone, add your KI (all of it, as is), stir like crazy, KBr precipitates, filter and rinse, evap, and as Gordon Ramsay would say, "Iodosafrole: done." No reflux, no dropping funnels, no bullshit. Just qualitative yield. It really is that simple.

As for the second step, take the others advice: use the hydrochloride salt, and add concentrated base. Using 40% is not adding a shitload of unnecessary water to the system - the Whole PointTM is to keep the reaction anhydrous - it's also a waste of perfectly good 40% methylamine. You lucky bastard :D.

And SN1, SN2, E2? Well, it's nice to think about those things - and it makes me feel better, because if you're talking reaction mechanisms, you probably aren't the average happy-go-lucky muppet who is going to blow himself up. But no less than a professor and head researcher of a university organic chemistry department once told me that working that shit out is what physical chemists are for... all she cares about is what works. One can take that the wrong way, of course, but I guess the point is that if you do the practical side of things right, then the molecules are still going to do their thing, whether you understand it or not. It's not bad advice.

V

jon

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Re: SN on iodosafrole with methylamine - TEST !
« Reply #28 on: April 11, 2011, 05:18:35 AM »
that has been tried it does'nt work do i need to stamp it onto your forehead so when you fuck it up you can go read it in the mirror?
bubble dry methylamine in.
or nuetralize it with triethylamine whatever suits you.

xxxxx

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Re: SN on iodosafrole with methylamine - TEST !
« Reply #29 on: April 11, 2011, 09:47:21 AM »
Would Triethanolamine also work for neutralizing the MeHN2 as it is also a strong organic base? Would the OH groups result in water being formed?

jon

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Re: SN on iodosafrole with methylamine - TEST !
« Reply #30 on: April 11, 2011, 10:17:50 AM »
no the oh groups might not interfere or they may that's where experimentation comes in.
water won't form from it it would behave as any other alcohol in solution.
trimethylamine would work too distill betaine to get it.
at the end you could probably wash it out with water.
i have'nt checked solubilities so don;t take my word in that.

mrhawke

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Re: SN on iodosafrole with methylamine - TEST !
« Reply #31 on: April 11, 2011, 11:45:48 PM »
Quote from: jon on April 11, 2011, 05:18:35 AM
that has been tried it does'nt work do i need to stamp it onto your forehead so when you fuck it up you can go read it in the mirror?
bubble dry methylamine in.

That is what I said... ;)

jon

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Re: SN on iodosafrole with methylamine - TEST !
« Reply #32 on: April 12, 2011, 12:26:42 AM »
i did'nt read it properly yes a lot of chemistry is over my head your'e right don't be concerned with what you don't know because you'll never understand it all anyway.
and yeah p-chem ugggh i don't think p-chemists actually do any lab work they just wrack thier brains with models and calculations.
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