Hunterman2244
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Iodine substituted flmodafinil
First post, but been lurking for a while and created an account recently.
I am looking to synthesize flmodafinil, with the fluorine substituted for iodine. I have not found any synthesis for flmodafinil, so I am asking for
help. Anyways it may differ. Can anybody help?
P.S. Smiles in case you want it:NC(=O)C[S](=O)C(C1=CC=C(I)C=C1)C2=CC=C(I)C=C2
Sorry for rambling lol
[Edited on 10-6-2018 by Hunterman2244]
[Edited on 10-6-2018 by Hunterman2244]
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Texium
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Thread Moved
10-6-2018 at 13:16 |
Texium
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Check out this thread if you haven't already: https://www.sciencemadness.org/whisper/viewthread.php?tid=61...
I won't take the time to draw out a whole scheme, but you should be able to figure out a way to walk it back to a point where you can synthesize
iodinated versions of the starting materials and work your way through that synthesis. The iodine substituents shouldn't cause problems.
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Hunterman2244
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I was looking at that, but couldn't figure out how to get the flourine on the phenyl group.
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Hunterman2244
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Not sure how to implement it, but could I use 4,4'- Dichlorodiphenylmethane as a building block? Then later substitute the chlorine to fluorine one
the final product or whatever.
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CuReUS
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1.Buy bis(4-iodophenyl)methanone (CAS -5630-56-8)
2.reduce to alcohol using dithionite- http://www.sciencemadness.org/talk/viewthread.php?tid=17051#...
3.react that with thioglycamide -http://pubs.acs.org/doi/abs/10.1021/jm00072a019
4.oxidise to sulphoxide using KMnO4's method -https://www.sciencemadness.org/whisper/viewthread.php?tid=61...
ammonium thioglycolate is known as perm salt-https://en.wikipedia.org/wiki/Ammonium_thioglycolate
You could heat the solution and distill out the thioglycamide 
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Hunterman2244
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I couldn't find anything on thioglycamide. I also don't have access beyond the first page of that article.
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clearly_not_atara
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I thought you wanted to use iodine instead of fluorine? There are various methods of fluorinating aromatic rings, but none should be necessary in this
case.
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Hunterman2244
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Quote: Originally posted by clearly_not_atara  |
I thought you wanted to use iodine instead of fluorine? There are various methods of fluorinating aromatic rings, but none should be necessary in this
case. |
I think that was a mistake, sorry.
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CuReUS
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That looks like sigma aldrich price.Try some chinese companies
| Quote: | | I could find the thioglycamide as mercaptoacetamide, but its $80 per gram |
I just told you an OTC source,you don't need to buy it from a chemical company
I finally worked out a decent synthesis of bis-iodo benzophenone
1.iodobenzene -http://www.orgsyn.org/demo.aspx?prep=CV2P0351
2.p-iodobenzoic acid-https://www.youtube.com/watch?v=3pJwfSaWHZg (PABA is available as supplement)
3.reacting p-iodobenzoyl choride with iodobenzene-http://www.nrcresearchpress.com/doi/10.1139/v80-406#.Wx9jYNI...
the acid choride could be generated in situ-https://www.sciencedirect.com/science/article/pii/S004040390...
I wonder if the whole thing could be done in one pot 
[Edited on 12-6-2018 by CuReUS]
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Bert
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After a brief look at the modafinil analogues, claimed effective dossage, anecdotal evidence on effects, particularly those which are ADD related.
Could you include some background or links to such on WHY you are seeking a particular modification of the molecules in question? I assume it isn't
mere intellectual curiousity, but don't have time to wade through the mix of research chemists, drug company hacks, stoners and desperate people just
trying to more effectively keep their shit together.
FYI, I've been prescribed Modafinil. Didn't seem to do much. Didn't even keep me awake.
Rapopart’s Rules for critical commentary:
1. Attempt to re-express your target’s position so clearly, vividly and fairly that your target says: “Thanks, I wish I’d thought of putting it
that way.”
2. List any points of agreement (especially if they are not matters of general or widespread agreement).
3. Mention anything you have learned from your target.
4. Only then are you permitted to say so much as a word of rebuttal or criticism.
Anatol Rapoport was a Russian-born American mathematical psychologist (1911-2007).
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Hunterman2244
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| Quote: Originally posted by Bert | After a brief look at the modafinil analogues, claimed effective dossage, anecdotal evidence on effects, particularly those which are ADD related.
Could you include some background or links to such on WHY you are seeking a particular modification of the molecules in question? I assume it isn't
mere intellectual curiousity, but don't have time to wade through the mix of research chemists, drug company hacks, stoners and desperate people just
trying to more effectively keep their shit together.
FYI, I've been prescribed Modafinil. Didn't seem to do much. Didn't even keep me awake. |
More or less intellectual curiosity.
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