dean-stark alternative

Aizstavis

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Mar 2, 2000, 3:00:00 AM3/2/00

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i want to turn a aldehyde into a primary amine, but dont have the equiptment
to do the dean-stark azotrope reaction to remove the water, are there any
other high yield alternatives, i thought i read something about using carbon
tetrachloride as the solvent and then as reaction occurs the water and CCl4
separate and therefore the reverse reaction cannot occur, anybody got any
ideas, thanks chad

Uncle Al

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Mar 2, 2000, 3:00:00 AM3/2/00

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NH3/NH4(+) aqueous buffer slightly on the acid side, NaBH3CN. What
drug are you presumably making?

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Aizstavis

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Mar 2, 2000, 3:00:00 AM3/2/00

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no drugs, im making a self-assembling monomer with the C=N-Me group on one
end, the lab is mainly phys chem/material science type stuff so not much
organic chem equiptment, and i think im making imine not amine, but thats my
fault, later

Uncle Al <Uncl...@hate.spam.net> wrote in message
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Uncle Al

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Mar 3, 2000, 3:00:00 AM3/3/00

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Which do you want, the imine or the amine? If you want the amine, how
alkylated do you want it? Look at the stuff in a KBr pellet in an
IR. Exocyclic N=C stretch is between 1620 and 1670 wavenumbers.

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Uncle Al
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Gabriel Tojo

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Mar 3, 2000, 3:00:00 AM3/3/00

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Aizstavis wrote:
>
> no drugs, im making a self-assembling monomer with the C=N-Me group on one
> end, the lab is mainly phys chem/material science type stuff so not much
> organic chem equiptment, and i think im making imine not amine, but thats my
> fault, later

So you want to make an imine by R-CHO + H2NMe gives R-CH=NMe + H2O.

Do you have activated molecular sieves in a Phys Chem Lab?. That´s all you need,
with almost any solvent:JOC, 41, 2000; JOC, 2657, 99, JACS 6958, 91.

Even MgSO4 could work: Tetrahedron, 6627, 93

Working with gaseous MeNH2 is going to be unconvenient. A solution in THF is
commercially available. Alternatively you may liberate the hydrochloride in situ
with a mild non nucleophylic base.

--
Gabriel Tojo
Profesor Titular de Quimica Organica
Royal University of Santiago de Compostela
SPAIN

Aizstavis

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Mar 3, 2000, 3:00:00 AM3/3/00

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So you want to make an imine by R-CHO + H2NMe gives R-CH=NMe + H2O

yes, that is the reaction im looking for

thanks for the help, its much appreciated, and sorry for the confusion, chad