What Solid Separates During the Malonic Ester Synthesis Reaction?

[ericvon11]

So I'm performing the reaction using:

urea + diethyl n-butylmalonate ----NaOEt---> n-butylbarbituric acid

My question is, after adding everything, you mix it and heat it, what is the solid that separates during this reaction? I've been thinking it might be diethyl n-butylmalonate but without 1 acid hydrogen due to the NaOEt. Why would this be unreacted though? ANY thoughts or advice would be greatly appreciated

 

[Nemus]

How about the sodium salt of the butylbarbituric acid?

 

[scorpion990]

There is a paper by Arthur W Dox and Lester Yoder called "Alkylbenzene Barbituric Acids." This was published in JACS in 1922. I found the answer in the experimental section. Look up the paper and give it a read.

I'm not trying to make you sweat... If you don't respond by tomorrow, I'll just post it here for completeness :)

EDIT: Didn't realize this was posted so long ago. Anyway... According to the paper, it's ammonium chloride. I assume you're running this reaction in ethanol.

 

[minerva]

It looks like you're talking about the non-professional synthesis of something which is either a controlled substance or pretty darned close to being a controlled substance... which is probably frowned upon by the admins around here.