Sciencemadness Discussion Board

2-(benzhydrylthio)acetic acid synthesis

pmanavado - 18-10-2017 at 00:32

Hello:
Does anyone know how i could go about making 2-(benzhydrylthio)acetic acid. I have searched the internet and was not able to find anything about it's synthesis.
I do appreciate all help

JJay - 18-10-2017 at 02:14

I'm not really sure what compound that is... what is the IUPAC name?

Chemi Pharma - 18-10-2017 at 02:50

Quote: Originally posted by pmanavado  
Hello:
Does anyone know how i could go about making 2-(benzhydrylthio)acetic acid. I have searched the internet and was not able to find anything about it's synthesis.
I do appreciate all help


This substance is a precursor to Modafinil and Andrafinil. There's a reference to it's synthesis at Rhodium pages, I am attaching below.

If you intend to synthesize Modafinil or Andrafinil there's easiest ways to do that without the need to make 2-benzhydrylthioacetic acid.

Do a search here at Sciencemadness and you will find a lot of references I'd posted some time ago in another thread.

There's another easy way to synthesize it starting from the Bunte Salt too, at prepublication section, written by KMnO4.



Attachment: modafinil V.pdf (204kB)
This file has been downloaded 632 times

j_sum1 - 18-10-2017 at 02:53

It looks like this:
https://www.scbt.com/scbt/product/2--diphenylmethyl-thioacet...

And I have no idea where to start.

JJay - 18-10-2017 at 03:19

Hm... diphenylmethyliodide would form a thioether with 2-thioethanol, which could then be oxidized with chromic acid. Benzophenone would probably be a good starting point.

Metacelsus - 18-10-2017 at 03:35

The chromic acid would likely oxidize the thioether to at least the sulfoxide (which might be OK given the intended final product) and possibly the sulfone (which would be unwanted). Source

I would recommend the Bunte salt method, which is described on this forum.

JJay - 18-10-2017 at 03:52

I'm pretty sure the thioether would oxidize slowly, especially in the cold, but the alcohol/aldehyde would react almost instantly in cold acetone.

CuReUS - 18-10-2017 at 07:01

Quote: Originally posted by pmanavado  

Does anyone know how i could go about making 2-(benzhydrylthio)acetic acid.

http://www.sciencemadness.org/talk/viewthread.php?tid=66274#...
Quote: Originally posted by Chemi Pharma  

If you intend to synthesize Modafinil or Andrafinil there's easiest ways to do that without the need to make 2-benzhydrylthioacetic acid.

really ?:o

Chemi Pharma - 18-10-2017 at 10:11

Quote: Originally posted by Chemi Pharma  

If you intend to synthesize Modafinil or Andrafinil there's easiest ways to do that without the need to make 2-benzhydrylthioacetic acid.[/rquote]
really ?:o


What I mean @Cureus is the fact you can do Modafinil and Andrafinil synthesis without producing benzhydrylthioacetic acid as an intermediate, such Rhodium's recipe done.

You can sinthesize the amide directly, starting from the same bromo-diphenyl-methane, like this:

modafinil 1.JPG - 21kB

Also, Via Bunte salt the intermediate formed is the amide and not the acid.

clearly_not_atara - 18-10-2017 at 11:06

So have we decided that modafinil is not recreational? Cool.

Thioglycolic acid is used in hair removers:

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

I believe that it can be converted to its amide by heating the ammonium salt, similar to other amide preparations. From thioglycolamide all you need to do is react with benzyhydryl halides and oxidize the resulting thioether.

As for the extraction of thioglycolate from hair removers -- perhaps you can precipitate the calcium salt "CaSAcO" and then liberate the thioglycolic acid with H2SO4.

CuReUS - 19-10-2017 at 05:02

Quote: Originally posted by clearly_not_atara  
As for the extraction of thioglycolate from hair removers -- perhaps you can precipitate the calcium salt "CaSAcO" and then liberate the thioglycolic acid with H2SO4.

ammonium thioglycolate is directly available as perm salt -https://en.wikipedia.org/wiki/Ammonium_thioglycolate