Thiolation to replace I on m-iodobenzylguanidine

  • Thread starter jjaynes
  • Start date
In summary: I on m-iodobenzylguanidine with -SH. He has successfully used this method before to replace a chloro on 4-chloropyridine. The process involves dissolving the N-oxide and Na2S in ethanol and refluxing for a week, followed by filtration and NMR confirmation. Jesse advises to try it on a small scale first and to consider the stability of the rest of the molecule under basic conditions. In summary, Jesse suggests using sodium sulfide for thiolation, with caution for the toxicity of Na2S and consideration for the stability of the rest of the molecule under basic conditions.
  • #1
jjaynes
3
0
I am trying to replace the I on m-iodobenzylguanidine with SH. Any ideas?

Jesse
 
Chemistry news on Phys.org
  • #2
You might be able to use sodium sulfide. I once replaced a chloro on 4-chloropyridine with -SH using sodium sulfide, but the details of the reaction escape me right now since I did it a real long time ago. I will look it up in my notebook tomorrow at work.
 
  • #3
thiolation

Thanks! I look forward to your reply.
 
  • #4
I actually did it on 4-chloropyridine N-oxide, so I don't know if it will work on your system or not since the N-oxide strongly activates the 4 position, but you can give it a shot.

15 g of the N-oxide and 18.6 g of Na2S were dissolved in 1000 mL of ethanol and were refluxed for 1 week. The solution was then filtered, rotavaped down, and washed with ether. NMR confirmed thiolation. Yields were difficult to determine because of the presence of inorganic salts.


If you do try it, do it on a small scale first. Na2S and all of the H2S it gives off are pretty toxic.

Also consider the rest of your molecule, Na2S in solution will turn the solution very alkaline, so the rest of your molecule must be stable under basic conditions for the reaction to work.
 
Last edited:
  • #5
Thanks so much. I'll give it a try.

Jesse
 

What is thiolation and how does it replace iodine on m-iodobenzylguanidine?

Thiolation is the process of replacing a hydrogen atom on a molecule with a thiol group (-SH). This can be done through various chemical reactions. In the case of m-iodobenzylguanidine, thiolation involves replacing the iodine atom with a thiol group, resulting in a molecule with a sulfur atom in place of the iodine.

Why would thiolation be used to replace iodine on m-iodobenzylguanidine?

Thiolation can be used to modify a molecule for various purposes, such as improving its solubility, stability, or binding affinity. In the case of m-iodobenzylguanidine, thiolation may be used to improve its ability to target specific receptors or to enhance its therapeutic effects.

What are the benefits of using thiolation instead of other methods to modify m-iodobenzylguanidine?

Thiolation offers several advantages over other methods of modifying molecules. It is a relatively simple and versatile process that can be performed under mild conditions, making it suitable for a wide range of molecules. Thiolation also allows for precise control over the position and number of modifications on the molecule.

Are there any potential risks or drawbacks to using thiolation to replace iodine on m-iodobenzylguanidine?

Like any chemical reaction, thiolation carries some risks, such as the potential for side reactions or the formation of unwanted products. Careful optimization and purification techniques can help mitigate these risks. Additionally, thiolation may alter the properties or behavior of the modified molecule, which could affect its safety or efficacy.

What are some potential applications of thiolation on m-iodobenzylguanidine?

Thiolation of m-iodobenzylguanidine may have a variety of applications in the fields of medicine and research. It could be used to improve the delivery of the molecule to specific tissues or cells, enhance its stability in the body, or modify its pharmacokinetic properties. Thiolation may also be used to create novel derivatives of m-iodobenzylguanidine with unique properties and applications.

Similar threads

Replies
23
Views
2K
Replies
5
Views
908
Replies
13
Views
2K
Replies
1
Views
206
Replies
2
Views
1K
  • Computing and Technology
Replies
30
Views
2K
Replies
6
Views
1K
  • Chemistry
Replies
3
Views
1K
Back
Top