ChemichaelRXN - 14-2-2020 at 09:32
Bromethiazole Synthesis (halogenation replacing hydroxy group)
This was a fun project. I made the HBr and then used it for this halogenation to get a high yield. (78%)
I started from Sulfurol
From 21.23g HBr / 80.91g/mol HBr x 1/1 x 143.207g/mol sulfurol = 37.5g sulfurol required. I added twice the amount of HBr as it makes the salt and you
require extra for the halogenation. I ended up heating the mixture for two hours and the temperature settles at 110c when heating.
My yield was 78%
To separate the bromethiazole, you must basify the solution to remove the HBr from bromethiazole.
21.23G HBr / 80.91g/mol x 1/1x 40g/mol of NaOH= 10.469g NaOH. I added a bit extra.
You must add NaCl to make a brine to separate it in the separatory funnel. Collect the freebase bromethiazole and for me it is for research only. I
will likely make the HCl salt and store the crystals as an accolade.
Fun project...here are some pictures!
[Edited on 14-2-2020 by Mr.StinkyGas]
[Edited on 14-2-2020 by Mr.StinkyGas]
[Edited on 14-2-2020 by Mr.StinkyGas]
[Edited on 14-2-2020 by Mr.StinkyGas]
Boffis - 15-2-2020 at 09:19
Interesting work, its similar to the preparation of 1,4-dibromobutane from butane-1,4-diol that I had posted previously. Where did you get your
sulfurol (2-(4-methyl-5-thiazolyl)ethanol) from and what are you planning to do with the resulting bromoethane derivative?
You could condense it with sodium iminodiacetate to give an interesting complexing agent 
ChemichaelRXN - 15-2-2020 at 10:16
Thanks! I will check out your project as well. This was actually my first halogenation reaction. It was a nice project that I might scale up. I have
3Kg of Sulfurol to use and bought the chemical from China for my company Syntharise. I dont have any plans other than making the salt form, maybe a
fumarate of it would be interesting and not so hygroscopic.
Also i am just wondering, do you know if sulfurol has any bioactivity on its own or only when you halogenate it? Not really sure. I noticed it was
sold for perfume use...it has a meaty smell, that would be an interesting perfume lol
[Edited on 15-2-2020 by Mr.StinkyGas]
ChemichaelRXN - 10-3-2020 at 13:36
Here is another synthesis you may find interesting, of Clomethiazole Hydrochloride. This time with conc. hydrochloric acid for chlorination, replacing
the sulfurol hydroxy group. I had a bunch of it so I used 210mL sulfurol based on density of 1.192g/ml and i used 290ml of conc. HCl. Very
straightforward. I will post some pictures of the rotovap’d crystals later on.
(Theoretical Yield is 345grams of the hydrochloride salt)
You will never get the chemistry out of me...i was raised with organic chemistry experience
[Edited on 10-3-2020 by Mr.StinkyGas]
ChemichaelRXN - 11-3-2020 at 13:20
And some extra pictures during and after completion!
arkoma - 5-6-2020 at 11:58
@Mr. Stinkygas
Would you U2U me please?