Author Topic: Hofmann Rearrangement Yields (Read 3632 times)

dingbow · « **Reply #60 on:** August 13, 2011, 03:39:42 AM »

Quote from: reDEEMed on August 13, 2011, 01:06:36 AM

Okay, the formation of my N-Chloramide is almost complete.

Did you get the cyanuric acid precipitate as per the reference?

Just read the reference you posted, this looks really promising... *Runs off to find some TCCA

EDIT: by the way, I have always used heat for the rearrangement. Incidently the time I got the highest yield of ~25%, I prepared a separate solution of ~70c base, dumped it all into the reaction and then heated to bring it to 70c.

EDIT: Just noticed the same reference, uses sodium bisulfite to convert the N-Chloramide back to the amide. Surely this would lower yields when the same reagent is used to quench excess hypochlorite that seems to be mentioned in the other refs? Could explain why I got so much amide precipitate last time I ran this.

reDEEMed · « **Reply #61 on:** August 13, 2011, 05:13:45 PM »

Yes, everything went the way I saw it going in my head before I started. I'm gonna say it was a success, we'll see how it goes adding this paste I now have to my Hoffman. Now I have to read more so I'm confident about the next step.

I know it has to irritate the fuck out of some of these dudes around here, I know they are just like "FUCKING DO IT ALREADY!!!" bwahahahaha

Edit:What happened to my beautiful amide!?!?!

Oh well...

akcom · « **Reply #62 on:** August 13, 2011, 05:30:13 PM »

Did you dry your methanol before hand? My choroamine was a white sticky solid

reDEEMed · « **Reply #63 on:** August 13, 2011, 05:33:52 PM »

Fuck no, that's what's going on, I know it is. God dammit.

Well, it shouldn't effect my next step, should it? Next time I will dry my methanol though. Fuck, I was in such a frenzy yesterday I made several stupid mistakes. Not the least of which cost me 10 grams of amide and almost killed me.

Edit: Regarding the use of PTCs-
Everything I've read about using fabric softeners has been negative. Not that any of those references have been specifically aimed at this exact situation, though. But almost without fail people called the quaternary ammonium salts used in fabric softeners useless because of their excessive chain length. Now, this means fuck all to me as I have no idea what that means and I currently don't have the spare brain power to dedicate to learning it. I did however wonder if anyone would be awesome enough to address that.

Something I did come across in reading about that is that most of these chemicals that are considered very good for use as a ptc are readily available in their pure form and not at all suspect. Why not just take a $100 and stock up on a few different ones?

dingbow · « **Reply #64 on:** August 14, 2011, 12:41:11 AM »

Given that the hofmann is run in an aqueous solution, It shouldnt be an issue, but could explain why you have a paste.

Did you remove your MeOH under vacuum? Try recrystalise?

dingbow · « **Reply #65 on:** August 14, 2011, 01:20:07 AM »

Quote from: akcom on August 13, 2011, 05:30:13 PM

Did you dry your methanol before hand? My choroamine was a white sticky solid

Could you provide a brief outline of your procedure? Have you rearranged the chloroamide?

reDEEMed · « **Reply #66 on:** August 14, 2011, 06:15:47 PM »

Success is bitter and makes you grind your teeth incessantly.

Why does a marquis turn bright red, though?

Enkidu · « **Reply #67 on:** August 14, 2011, 09:24:50 PM »

It's possible that you only have one stereoisomer of MDA.

lugh · « **Reply #68 on:** August 14, 2011, 11:03:54 PM »

The Marquis reagent can mean many things:

http://www.cognitiveliberty.org/shulgin/adsarchive/marquis.htm

http://www.erowid.org/chemicals/mdma/mdma_faq_testing_kits.shtml

http://en.wikipedia.org/wiki/Marquis_reagent

Wizard X · « **Reply #69 on:** August 15, 2011, 12:25:24 AM »

Use TLC first, and then the Marquis reagent. This gives greater accuracy and identification.

Quote

As the test is extremely sensitive, no estimate can be easily made as to the quantity of alkaloid present. And of course, a dark color will tend to hide a light color. As with all assays requiring subjective interpretation, experience is everything.

-- Dr. Shulgin

reDEEMed · « **Reply #70 on:** August 15, 2011, 02:26:09 AM »

Bottling up what I have to get a final number on yield of whatever it is I have and trying again.

Edit: Will do the chloramide conversion again, but with strict attention to anhydrous conditions, especially the methanol. Fuckin' shit, I heated up my flask and all that shit to around the temperature of the sun to dry it and forgot all about the methanol. This has impressed upon me the need to print out check lists, which I will do from now on.

I just put 20gms of amide in to try Java's cold method word for fucking word. Yes, I printed out a checklist.

Jeezus fucking christ can I borrow a dollar from one of you guys?

fries · « **Reply #71 on:** August 15, 2011, 07:53:16 AM »

how did you clean the result? What colour did it end up?

dingbow · « **Reply #72 on:** August 15, 2011, 11:29:35 AM »

maybe obtain the MP of the hydrochloride you have obtained for assurance. Keen to hear what your yield was from amide to amine.

I'll give it a go either way, but first im going to try my hand at monomethylation..

fries · « **Reply #73 on:** August 15, 2011, 12:39:23 PM »

Quote from: dingbow on August 15, 2011, 11:29:35 AM

I'll give it a go either way, but first im going to try my hand at monomethylation..

I'd like to hear your results on that - I have paraformaldehyde, but nothing to reduce formaldehyde imine with...

reDEEMed · « **Reply #74 on:** August 16, 2011, 05:29:44 PM »

Quote from: Wizard X on August 15, 2011, 12:25:24 AM

Use TLC first, and then the Marquis reagent. This gives greater accuracy and identification.

Quote
As the test is extremely sensitive, no estimate can be easily made as to the quantity of alkaloid present. And of course, a dark color will tend to hide a light color. As with all assays requiring subjective interpretation, experience is everything.

-- Dr. Shulgin

I know it sounds stupid but I didn't know tlc was something you could do at home. Now that I'm reading more about doing it specifically at home I had to come back and thank you for stating what is no doubt the obvious to you guys, but news to me.

Thanks!

Edit: I'm going to follow this guide for making the plates http://www.scienceprojectlab.com/plates-for-cromatography-science-project.html

Any clue which solvent would be best for this? I'm not opposed to trying several, but thought someone might already know one that works well.

Edit 2: I'm the edit king, hands down. I just saw this and thought that others might find it useful. Especially when evaluating different methods of this reaction we're talking about.

Recommended methods for the identification and analysis of amphetamine, methamphetamine and their ring-substituted analogues in seized material

Wizard X · « **Reply #75 on:** August 17, 2011, 12:13:13 AM »

Quote from: reDEEMed on August 16, 2011, 05:29:44 PM

I know it sounds stupid but I didn't know tlc was something you could do at home. Now that I'm reading more about doing it specifically at home I had to come back and thank you for stating what is no doubt the obvious to you guys, but news to me.

Thanks!

Edit: I'm going to follow this guide for making the plates http://www.scienceprojectlab.com/plates-for-cromatography-science-project.html

Any clue which solvent would be best for this? I'm not opposed to trying several, but thought someone might already know one that works well.

Edit 2: I'm the edit king, hands down. I just saw this and thought that others might find it useful. Especially when evaluating different methods of this reaction we're talking about.

Recommended methods for the identification and analysis of amphetamine, methamphetamine and their ring-substituted analogues in seized material

Glad your learning!

Look on Youtube for video examples of TLC.

http://www.youtube.com/results?search_query=thin+layer+chromatography&aq=0&oq=thin+layer

Thin Layer Chromatography Demonstrated by Mark Niemczyk, PhD http://www.youtube.com/watch?v=w0FyQ_tO15U

reDEEMed · « **Reply #76 on:** August 17, 2011, 05:02:42 AM »

I did figure one thing out about the crystal I had. it was much lighter than I thought. What I thought were solid point sized finger licks were nothing more than 10-20mg. I weighed out .100mg earlier today and I'm still fucked off my rocker.

BTW, any idea where I could get one of those uber smart fuckin' monkeys?

Edit: You know what occurs to me about blahblahblah's monkey method, it's actually worth stating as I believe from what I've read and heard that yields from the Hoffman go up with batch size and not linearly. Not only does it seem to scale up well, it seems to prefer it. This monkey and his several kilos of amide no doubt has a much easier time than those of us doing 10-20gms at a time. I'm going to do the next one with at least 40gms and see what's up with that. I plan on using a spider monkey as I feel the smaller monkey may have some synergistic effect on the smaller batch size.

Sedit · « **Reply #77 on:** August 17, 2011, 09:27:37 PM »

I am experimenting and have been for a few months now with various papers to do Paper chromatography at home. I have been able to achieve pretty good results with a hydrophobic water color paper from the art store but I'm still having issues where there can be a heavy run together between compounds.

This may not be the paper but might have more to do with technique. I think the spot has to be super small on paper else the run together is much more noticeable. Also the RF values and the solvent systems I think need to be much different then when using Silica gel. All in all its not going bad and when I am able to produce repeatable decent results I will no doubt write a report here because I really want to see more people post analysis of there reactions more then just saying.... "WOW im HiGh"...

.

It will greatly enhance our cause and our site if this goes well.

akcom · « **Reply #78 on:** August 17, 2011, 11:26:43 PM »

Whatman filter paper is a decent substitute for TLC plates. Silica plates are not that expensive. 100 dollars gets you a fucking ton. You can use a nail filer for scoring them, although a real TLC plate scorer is the best option

dingbow · « **Reply #79 on:** August 18, 2011, 11:10:25 AM »

did you ever figure out your yield with the TCCA route, from amide to amine?

Author Topic: Hofmann Rearrangement Yields (Read 3632 times)

dingbow

Re: Hofmann Rearrangement Yields

reDEEMed

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akcom

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reDEEMed

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dingbow

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dingbow

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reDEEMed

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Enkidu

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lugh

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Wizard X

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reDEEMed

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fries

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dingbow

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fries

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reDEEMed

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Wizard X

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reDEEMed

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Sedit

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akcom

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dingbow

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