Synthesis of Diazald
Diazald is N-methyl-N-nitroso-p-toluenesulfonamide.
I think it would be prepared by nitrosating N-methyl-p-toluenesolfonamide with H2SO4/NaNO2.
Diazald is used for preparing Diazomethane by reaction with NaOH in alcohol.
Using Nitrosomethylurea (easily prepared, look in orgsyn) for diazomethane production is the traditional method, but nitrosomethylurea is a REALLY
nasty substance, very highly carcinogenic.
Hence I want to prepare the much less dangerous Diazald myself.
I would do it like this:
1- React tosyl chloride with aqueous methylamine solution.
2- React the resulting N-methyltosylamide with NaNO2/H2SO4.
My questions would be the following:
Is N-methyltosylamide sparingly soluble in water so that it could simply be isolated by filtering after its synthesis?
What would be the best method for the subsequent nitrosation of the substance so that pure Diazald can be isolated?
I would be very happy if one could provide me with a lab procedure for the synthesis of N-methyltoluenesulfonamide and Diazald.
EDIT:
Nevermind, I found it:
http://www.orgsyn.org/orgsyn/prep.asp?prep=cv4p0943
I was under the impression that no instructions for the preparation of this compound were available on the web. Also, I did not try different spelling
of the compound.
[Edited on 2-7-2007 by garage chemist]
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