[whawhaxd]

Hi, I'm running the reaction (pic attached) in three different solvents, DCM, Acetonitrile, and Ethanol.

I don't know why I'm not really getting what I expect.

So, my question is,

is there any other possible path for this reaction to take, rather than the one drawn?

Also, what solvent would you choose?

Thank you for your time guys!

[Wisemanleo]

What are you getting instead?

[Mitch]

If it is an Sn2 reaction from what I expect, would a polar protic solvent like ethanol work best or a nonpolar aprotic solvent like chloroform work best?

[mahesh]

What are the reaction conditions that you are using? and what is the product profile? how much conversion are you getting?

[Donphil07]

may be, your reaction need a condition without water, you much purificate sovel before start your work. you can disill sovel by CaH2 or Dean-stark trap. Have sucessful!

[sjb]

Do you need it di-Boc'd, or are you after benzyl guanidine itself?

Does http://www.wikipatents.com/gb/606181.html (example help any?

S

[alphahydroxy]

OK, after a (very!) brief scan of this paper:

Tet. Lett. (1998), 39, 1565

It appears that with 2 equivalents of benzylamine you can get a double addition product arising from an initial addition-elimination to give the product you want, followed by elimination of a t-BuO- group to give the isocyanate, and subsequent addition of a second equivalent of the amine to yield the amidinourea.

They do the reaction for 8 hours in refluxing THF. The indication is that with strictly stoichiometric amounts of amine, the mono-addition product can be easily obtained.

[sjb]

Do you need it di-Boc'd, or are you after benzyl guanidine itself?

Does http://www.wikipatents.com/gb/606181.html (example help any?

S

Sorry, that's example 7+1 (with apologies to Wizzards, Rincewind and Pratchett)

[agrobert]

I recommend refluxing the reaction in a suitable solvent and adding a base that can work as a catalyst for the addition-elimination reaction that is taking place.  Good catalytic organic bases are triethylamine(TEA) or 4-(dimethylamino)-pyridine (DMAP).