Author Topic: Short Questions Thread  (Read 10820 times)

Evilblaze

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Re: Short Questions Thread
« Reply #440 on: March 29, 2010, 09:59:53 PM »
Start form alanine, HNO3/HCl to the 2-chloropropionic acid, S/Cl2 to the acid chloride. UTSE for experimental details.

I know that method. Even the diazotation of aniline and sandmeyer reaction is also on the list, but aniline is not so cheap. Instead of the lactic acid, so it would be preferred to use that...

Enkidu

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Re: Short Questions Thread
« Reply #441 on: March 30, 2010, 02:33:26 AM »
When forming a Grignard reagent from an alkyl halide and Mg, what keeps the newly formed reagent from just immediately reacting with other alkyl halide molecules to form di-alkyls?

I think you need a lewis acid.

Quote from: Evilblaze
I know that method. Even the diazotation of aniline and sandmeyer reaction is also on the list, but aniline is not so cheap. Instead of the lactic acid, so it would be preferred to use that...

No one said anything about aniline, which is aminobenzene. I'm talking about alanine, which is very cheap. Alanine is $30/kg. Exactly how are you going to get that thionyl chloride? It will be expensive any way you do it. Sandmeyer will be expensive and low yielding... so it is not on the list.

You'll know when the reaction is done if you follow it by TLC. You should do that the first time you run any rxn that you don't have experimental details on in order to optimize it. Just check in Vogel for a general procedure for the for the chlorination at each position, and reflux for the longer length of time.
« Last Edit: March 30, 2010, 02:43:48 AM by Enkidu »

Vesp

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Re: Short Questions Thread
« Reply #442 on: April 01, 2010, 12:09:16 AM »
When molten, would anhydrous calcium chloride, or other molten chloride salts act as a solvent, and dissolve other salts?

If they do, it would seem to me that perhaps aluminum sulfate could be dissolved in calcium chloride, or a mix of chloride salts -- I think this would be useful in producing AlCl3.

If I had time, I'd just try it. :(
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Enkidu

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Re: Short Questions Thread
« Reply #443 on: April 06, 2010, 10:10:23 AM »
Quote
ning
(acetaminophanatic)
04-16-04 22:15
No 501222

BTW, ning doesn't know if this has been done at the hive already, but you can knovenagel condense 3,4,5-TMB with acetonitrile as well as nitromethane. If the double-bond is reduced, then a hoffmann rearrangement will nicely yield a phenethylamine. Refs if desired.

Does anyone have said refs?

Enkidu

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Re: Short Questions Thread
« Reply #444 on: April 07, 2010, 08:15:15 AM »
^ erm, anyway, you cna't make amphetamines with any kind of a Knoevenagel reaction besides the Henry, as far as I can tell. If acetonitrile is used to make a phenethylamine, a strong base must probably be used. If it could be done with a hydroxide, it might be useful, but I bet the base will have to be stronger than that.


On to my new query, does anyone have a ref that details the synthesis of gbl from ghb by boiling in dilute mineral acid?

SOMA

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Re: Short Questions Thread
« Reply #445 on: April 07, 2010, 10:35:27 PM »
To make the acyl chloride of 2-chloropropionic acid, reflux S2Cl2 with a catalizing ammount of iodine. More info on the hive at a thread by antoncho on the making of acetic anhydride from sodium acetate and S2Cl2.

NeilPatrickHarris

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Re: Short Questions Thread
« Reply #446 on: April 09, 2010, 01:14:39 AM »
i'm trying to figure out the molecular weight and formula for the primary amide of MDA. i've never attempted anything like this before so forgive me if i'm way off.  the primary amine R-NH2 to primary amide R-C(O)NH2. take the molecular weight of the primary amine (MDA) and add 1 carbon atom and 1 oxygen atom

179.22 + 12.0107 + 15.9994 = 207.2301 g/mol
....which is mda's molecular weight + carbon + oxygen

MDA: C10H13NO2
Amide: C11H13NO3

is that right?

Naf1

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Re: Short Questions Thread
« Reply #447 on: April 09, 2010, 01:35:14 AM »
Thats right, you are going to add 28.0101g/mol

A good way to confirm if you are ever a bit unsure, look for known examples. For example; Anilines molecular weight compared to Benzamides, both are freely available at wiki.


NeilPatrickHarris

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Re: Short Questions Thread
« Reply #448 on: April 09, 2010, 01:44:48 AM »
cool, thanks Naf1

Sedit

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Re: Short Questions Thread
« Reply #449 on: April 09, 2010, 01:47:05 AM »
A good way to do it is stop wasting time adding Carbon chains and draw the shit in ChemSketch and tell it to spit out the formula, weight, name....ect..ect... refractive index for that matter hell.

Point is Get ADC chemsketch and save yourself alot of time.

I would post an example but my image editor is all fucked up.
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Naf1

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Re: Short Questions Thread
« Reply #450 on: April 09, 2010, 02:01:45 AM »
Or you could do that! But is nice to know how to do it without software also.

timecube

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Phenylalanine to amphetamine or N-methylamphetamine
« Reply #451 on: April 09, 2010, 03:16:43 AM »
Split from Phenylalanine to amphetamine or N-methylamphetamine - Enkidu

I started thinking about routes from phenylalanine last night, and something occurred to me that for whatever reason I hadn't considered before.

Why can't we go from phenylalanine to phenylacetaldehyde via strecker degradation.. and then just oxidize it to phenylacetic acid and go from there?

I'm sure I'm missing something.
« Last Edit: April 09, 2010, 06:46:33 AM by Enkidu »

java

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Re: Phenylalanine to amphetamine or N-methylamphetamine
« Reply #452 on: April 09, 2010, 03:28:23 AM »
I started thinking about routes from phenylalanine last night, and something occurred to me that for whatever reason I hadn't considered before.

Why can't we go from phenylalanine to phenylacetaldehyde via strecker degradation.. and then just oxidize it to phenylacetic acid and go from there?

I'm sure I'm missing something.

..........yes , you're working backwards, instead of getting a single isomer product, you're going towards an ugly route with a recemic product......java
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Naf1

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Re: Phenylalanine to amphetamine or N-methylamphetamine
« Reply #453 on: April 09, 2010, 04:02:02 AM »
Java is right, I have actually talked about that method before (and still think it does have some merit). It is posted on the first page just so you dont have to go back here is the quote;

"Phenylalanine can be treated with nitrous acid to produce phenyllactic acid, nitrous acid is produced from sodium nitrite and any mineral acid. Phenyllactic acid can then be treated with Lead tetra acetate (made with red lead oxide and glacial acetic acid) and will yield around 58% phenylacetaldehyde.

http://www.journalarchive.jst.go.jp/jnlpdf.php?cdjournal=bcsj1926&cdvol=9&noissue=1&startpage=8&lang=en&from=jnlabstract

Strecker degradation of phenylalanine with sodium hypophosphite should return a better yield of phenylacetaldehyde than the procedure above.
Also alpha methylation of phenylalanine as previously discussed after strecker degradation yields phenylacetone.

http://www.erowid.org/archive/rhodium/chemistry/p2p.strecker.html

With phenylacetaldehyde in hand one would proceed to gas with methylamine to create the schiffs base, which could be dripped into methyl magnesium iodide to produce a modest (40%+) yield of racemic methamphetamine."

NeilPatrickHarris

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Re: Short Questions Thread
« Reply #454 on: April 09, 2010, 04:06:31 PM »
A good way to do it is stop wasting time adding Carbon chains and draw the shit in ChemSketch and tell it to spit out the formula, weight, name....ect..ect... refractive index for that matter hell.

Point is Get ADC chemsketch and save yourself alot of time.

I would post an example but my image editor is all fucked up.

dude... thanks for turning me onto this!  i grabbed chemsketch (freeware version) and played around with it a little bit but then i got ChemBioDraw Ultra 11.0 from the ChemBioOffice2008 suite and liked that one a little bit more.  i'm amazed at all the shit it can do, i drew up the amide and made it 3d, etc, fucking cool.  i've been missing out by not playing with this type of software sooner.  my only gripe i have is that the bp, mp are pretty far off.  for example i drew a molecule that i already knew these properties of, i drew safrole and it said the bp was 527K (254C) instead of 234C and it said the mp was 327K (54C) instead of 11C.  apparently "ChemBioDraw does not store literature values for these properties like a database program. It is actually predicting these values based on a variety of mathematical algorithms. These calculations are subject to discrepancies from literature values. For more information about the methods used for calculating these values, please refer to the Help menu or User's Guide." <- per h**p://www.cambridgesoft.com/services/DesktopSupport/KnowledgeBase/TechNotes/details/Default.aspx?TechNote=972

oh well, still an impressive program
« Last Edit: April 09, 2010, 04:36:40 PM by NeilPatrickHarris »

Sedit

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Re: Short Questions Thread
« Reply #455 on: April 09, 2010, 05:44:45 PM »
Yeh I argree I ran into this a while back but its still useful no doubt.
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You pissed off the wasp now enough is enough!!!

java

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Re: Short Questions Thread
« Reply #456 on: April 12, 2010, 02:38:07 AM »
found a can of a light brown paste that smells like cinnamon.....it doesn't dissolve in acetone or ethanol and in alkaline solution no base is released. has a MP above 200?C not soluble in chloroform also......any ideas.....java
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Sedit

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Re: Short Questions Thread
« Reply #457 on: April 12, 2010, 02:49:05 AM »
Any more details on the can?

I would evaporate the Et2O or EtOH and see if there is any cinnamaldahyde present. There the possibility that the cinnamon oil is present in some kind of base formula for whatever application it has to aid in its use.

The fact that you say it has a defind melting point is interestin though to say the lest.
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heisenberg

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Re: Short Questions Thread
« Reply #458 on: April 12, 2010, 03:28:07 AM »
Does anyone know how a methyl group on the aniline ring of a fentanyl effects the activity?
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Naf1

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Re: Short Questions Thread
« Reply #459 on: April 12, 2010, 03:42:14 AM »
Piperidine is condensed with o-flouroaniline to produce the flouro substituted product, ocfentanil which is slightly more potent than its parent fentanyl. (if that helps?)

I think a valid target should be ohmefentany, it is easier to synth than carfentanyl but comparable in potency;

Ohmefentanyl (beta-hydroxy-3-methylfentanyl) is an extremely potent analgesic drug which selectively binds to the µ-opioid receptor.
Ohmefentanyl is one of the most potent u-receptor agonists known, comparable to super-potent opioids such as carfentanil and etorphine which are used for tranquilizing large animals such as elephants in veterinary medicine. In mouse studies, the most active isomer 3R,4S,?S-ohmefentanyl was 28 times more powerful as a painkiller than fentanyl, the chemical from which it is derived, and 6300 times more effective than morphine.[1]. Ohmefentanyl has three stereogenic centers and so has eight stereoisomers, which are named F9201-F9208. Researchers are studying the different pharmaceutical properties of these isomers.[2].
The 4"-fluoro analogue of the 3R,4S,?S isomer of ohmefentanyl is the most potent opioid yet discovered, possessing an analgesic potency approximately 18,000-fold greater than morphine.
from wiki.
« Last Edit: April 12, 2010, 03:53:37 AM by Naf1 »