What Solid Separates During the Malonic Ester Synthesis Reaction?

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The discussion centers on the synthesis of n-butylbarbituric acid from urea and diethyl n-butylmalonate using sodium ethoxide (NaOEt). The main inquiry is about the solid that separates during the reaction after mixing and heating the components. Initial speculation suggests it could be diethyl n-butylmalonate, potentially lacking one acidic hydrogen due to NaOEt. However, a reference to a paper by Arthur W. Dox and Lester Yoder indicates that the solid is actually ammonium chloride, with the synthesis likely occurring in ethanol. The conversation also hints at the sensitivity surrounding the synthesis of substances that may be controlled or closely regulated.
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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
 
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How about the sodium salt of the butylbarbituric acid?
 
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.
 
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.
 
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