Re: ORGLIST:TLC of Nitriles

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From: Vijay Sane (vsane$##$hotmail.com)
Date: Tue Nov 11 2003 - 09:15:57 EST

Hello all

sorry for late reply as I was away. Having read both  mails, what I noticed is the compound formed may be still in it's hydrochloride salt form and hence water soluble.

Mark how about this one, filter off the KCl formed ( if it is soluble, then evaporate to remove MeOH, t-BuOH under vacuum. now add some polar solvent like EDC or MDC to dissolve organics and now filter off KCl ) and then concentrate to remove solvents.

You can easily check the GC of the residual portion as it will have the raw materials and products ( or can check in presence of solvents before concentration ).


 regards

Vijay Sane

>From: Sharon Stone-Elander
>To: researchstuff@bellsouth.net, everybody@orglist.net
>Subject: Re: ORGLIST:TLC of Nitriles
>Date: Mon, 03 Nov 2003 16:35:02 +0100
>
>Hello Mark,
>Fluorbenzonitrile is volatile. When we've labelled it with fluorine-18, eluted on a TLC plate and immediately scanned for product with a radioTLC scanner, only the nonvolatile fluoride was detected. However, the fluorobenzonitrile had actually been formed in >80% conversions, as was shown by SPE procedures followed by radio-HPLC characterization of the eluent. The nitrile apparently completely disappears from the TLC plate during elution and subsequent drying /scanning.
>
>Chances are this is the reason you've been unable to visualize the fluorobenzonitrile.
>
>with greetings,
>Sharon Stone-Elander
>
>At 00.00 -0500 03-10-31, researchstuff@bellsouth.net wrote:
> > Hello everyone,
> >
> > Does anyone know of a TLC stain to visualize nitriles? I have tried vanillin, KMnO4, Iodine, and PMA, and neither worked. The reagent that I need to monitor in a reaction is fluorobenzonitrile.
> >
> > Thanks for any help.
> >
> >Mark
> >
>--
>++++++++++++++++++++++++++++++++++++++++
>Sharon Stone-Elander, Ph.D.
>Professor of Medicinal Radiochemistry, Karolinska Institute
>Department of Clinical Neuroscience, Positron Emission Tomography
>Mailing address:
>Karolinska Pharmacy, Karolinska Hospital, S-171 76 Stockholm, Sweden
>Email: sharon.stone@ks.se; Tel. +46 8 5177 53 31; Fax. +46 8 30 73 46
>++++++++++++++++++++++++++++++++++++++++
>_______________________________________________
>ORGLIST - Organic Chemistry Mailing List
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From : 
<researchstuff@bellsouth.net>
 
To : 
<everybody@orglist.net>
 
Subject : 
ORGLIST:Separation of Organic Compound from Aqueous Solution
 
Date : 
Tue, 4 Nov 2003 0:01:45 -0500
 
 Reply  Reply All  Forward  Printer Friendly Version
 
Hello All:

   I think I have made a 4-fluorobenzamidine derivative, more specifically,
N'hydroxy,N'methyl-4-fluorobenzamidine. The problem is that I can't extract it
from the aqueous phase. I am thinking the hydroxy and fluoride moieties of the
amidine are hydrogen bonding with water, thus enhancing its aqueous solubility.
Aqueous work-up is necessary for the separation because another salt (KCl)and
t-butyl alcohol are produced in the reaction and need to be isolated from the
product. I have tried extractions with the usual solvents: CH2Cl2 and ethyl
acetate. A TLC of the aqueous phase shows the presence of an organic compound. 

   Well, in an case, has anyone ever extracted aqueous soluble organic
compounds? Or know of a reference to this type of extraction.

   By the way, if this helps, I am running the reaction in methanol. I am
reacting 4-fluorobenzonitrile, methylhydroxyamine-HCl and tBuOK. For the
work-up: the solvent is evaporated, water added, followed by extraction with the
organic solvents mentioned above. 

 Thanks for any guidance here.
  
Mark


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