Re: ORGLIST:Carbamate reaction

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From: S.BARTOLI$##$soton.ac.uk
Date: Thu Oct 28 2004 - 11:11:53 EDT


Dear Jai,
you can form the isocyanate of your amine using triphosgene and
triethylamine. The reaction takes 10 mins to get to completion. The
important thing is that you must get rid of the excess of triphosgene after
the formation of the isocyanate. You can probably purify the isocyanate by
Flash cromatography without using MeOH.
Add then your N-Boc-ethanolamine and reflux.
It may require several hours, but it works.
Good luck.

Sandra

Scrive Jai Prakash <jpbans$##$rediffmail.com>:

> Hello everybody,
>
> I want to make a carbamate linkage between amine group of
> 2,6-dimethoxy aniline and hydroxyl group of N-Boc-ethanolamine.
> Firstly, I tried to activate N-Boc-ethanolamine with
> p-nitrophenylchloroformate and then reacted with 2,6-dimethoxy
> aniline in the presence of base. But it did not work out.
> Then, secondly, I activated 2,6-dimethoxy aniline with
> p-nitrophenylchloroformate and then reacted with
> N-Boc-ethanolamine in the presence of base. But still it is not
> formed.
> As such I am not a chemist by profession so there can be some
> lacking points. So I would appreciate if somebody can suggest me
> the right way to do this kind of synthesis. If there is another
> way to do this reaction, please let me know.
> Thanking you in advance,
> Regards,
> Jai
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