Re: ORGLIST: Alkylation of Semicarbazide

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From: AMGrainger$##$aol.com
Date: Fri Nov 23 2001 - 09:18:05 EST



Juan,

My few minutes of thought on this is that its a tough call.
I would start with an Alkylhydrazine - then you have to protect
the primary amine group somehow.
Then with the right protecting group, do phosgene and reaction
of inter acid chloride with ammonia.
Then you have to spring the free amine by deprotection.

Seems to be a number of steps.
Regarding alkylation procedure you mentioned. my guess is
you'd get a mixture of products because the secondary amine
is not sufficiently different in basicity to the other amine functions.
Even if you get some of what you want it would be v.difficult to fish
it out with distillation or chromatography or something.
Don't know if this is useful, but anyway my thoughts.

Regards,

Andy Grainger

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