Sciencemadness Discussion Board

Iodine substituted flmodafinil

Hunterman2244 - 10-6-2018 at 13:11

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]

Texium - 10-6-2018 at 13:23

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.

Hunterman2244 - 10-6-2018 at 13:30

Quote: Originally posted by Texium (zts16)  
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.

I was looking at that, but couldn't figure out how to get the flourine on the phenyl group.

Hunterman2244 - 10-6-2018 at 14:18

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.

CuReUS - 10-6-2018 at 23:45

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 :)

Hunterman2244 - 11-6-2018 at 08:38

Quote: Originally posted by CuReUS  
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 :)

I couldn't find anything on thioglycamide. I also don't have access beyond the first page of that article.

clearly_not_atara - 11-6-2018 at 12:25

Quote: Originally posted by Hunterman2244  
Quote: Originally posted by Texium (zts16)  
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.

I was looking at that, but couldn't figure out how to get the flourine on the phenyl group.

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.

Hunterman2244 - 11-6-2018 at 12:42

Quote: Originally posted by clearly_not_atara  
Quote: Originally posted by Hunterman2244  
Quote: Originally posted by Texium (zts16)  
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.

I was looking at that, but couldn't figure out how to get the flourine on the phenyl group.

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.

CuReUS - 11-6-2018 at 21:28

Quote: Originally posted by Hunterman2244  
bis(4-iodophenyl)methanone is like $700 a gram so nope.

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:P

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 :D

[Edited on 12-6-2018 by CuReUS]

Bert - 12-6-2018 at 08:23

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.

Hunterman2244 - 12-6-2018 at 09:03

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.