Dear Souvik, I know only one good method. It does use triflic azide, the problem is that TfN3 when dry is explosive... So I can not recommand this type of reagent if you never used it. Now question are you locked with an amine? Can you start for a different starting material?
How are you preparing TfN3? I started preparing this from triflic anhydride but the yield was very much low...
Dear Maxime, if possible send me the paper...
Maxime, as per I know that NaN3 can be used to convert aromatic amine into azide, but not for aliphatic azide...later I can send you one paper published in organic letter where thay have used indole azide to convert aliphatic amine to aliphatic azide...but I have not yet used this reagent in my studies...
Guys, TfN3 has and will work but it is a very dangerous reagent, it can be explosive and will if dry. Some accidents have been reported and in the lab. next door to me few year ago it did! Again if you have not used it before or you can not be properly suppervised, I would not touch it!
Thank you Mr. Bornaghi...As I have not used it before, I will think again before using it. Can you suggest any other reagent??
Sorry I do not know. search this site for similar reaction, another member mentionned another reagent few weeks ago.. you might want to contact hin for some details/safety guide line.
I don't think you can convert an amine to an azide; you have to go in the other direction. You can convert an amine to a diazonium salt: just don't let the salt dry out or it becomes explosively unstable. The standard syntheses of azides are substitution of a tosylate or Bromide with the azide anion. The primary amine can be most readily formed using 1.5 equivalents of a lithium aminoborohydride at room temperature. I recommend lithium dimethylaminoborohydride because the resulting dimethylamine is easily removed.
Aminoborohydrides. 8. A Facile Reduction of Aliphatic and Benzylic Azides to the Corresponding Amines in High Yield and Purity Using Lithium Aminoborohydrides
Salvador G. Alvarez, Gary B. Fisher, and Bakthan Singaram
Tetrahedron Lett. 1995, 36, 2567
Hello Souvik,
You can try Imidazole-1-sulfonyl Azide Hydrochloride reagent to do the transformation (It is very easy to prepare).
Ref: http://pubs.acs.org/doi/pdf/10.1021/ol701581g
Hope it will work out.
Imidazole-1-sulfonyl Azide Hydrochloride, is a very safe reagent. We are using it very frequently in our lab. If you keep it at -20 deg C it is stable for more than a year.
Hi there, I have also been trying to do amine-azide interconversion recently and its not really straight forward. In our attempts we also tried diazotransfer reaction on aliphatic amine using catalytic CuSO4 and NaN3 in DCM/H2O/Methanol solvent at room temperature but no reaction progress was observed within 24 hrs. When increasing the temp by 10deg, we observed decolourization and we are hoping it is what we are expecting....have a look at JACS, 2002, 124, 10773-10778, it might help, let us know what worked for you since we are on the same boat.
Is it possible to do the conversion after making the amine functionality into a good leaving group such as N-tosyl and then reaction with sodium azide? I think I should try once in this method.
No, it will not work. Have a read:
http://www.organic-chemistry.org/namedreactions/nucleophilic-substitution-sn1-sn2.shtm
it will help you understand SN1 and 2
Souvik, that's exactly the way to do the transformation. The experimental details about synthesizing several different types of azides, including axial and equatorial steroidal azides (I'm referring to the orientation of the N3 group) are given in the Tett Lett paper I referenced in my first reply to you. If you have difficulty finding the paper, let me know and I'll create a pdf attachment with the procedures and send it to you.
Great! Let me know if the procedures make sense or if you need any more info.
Hello Fisher and Souvik,
Can you send me the full PDF of paper or detail to convert aliphatic amine to aliphatic azide??
Dear Friends
I am currently running a diazo transfer reaction with TfN3 in toluene but my question is about the stability of TfN3 to water? Do you have any details you could share with? Publication?
Best regards
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