Question

Amobarbital is a sedative marketed under the trade name Amytal. Propose a synthesis of amobarbital, using diethyl malonate and ureaas two of the starting materials.

Short answer

Synthesis of Amobarbital using diethyl malonate and urea is shown below.

Step-by-step solution

Amobarbitual characteristics

Amobarbitual, a barbiturate is also known as 5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione.It is a CNS[l1] depressant.

Synthesis of Amorbarbital

Diethyl malonate treated with aldol, followed by reaction with ethyl bromide, gives diethyl 2-ethylmalonate. This compound then reacts with 1-bromo-3-dimethyl propane to obtain diethyl 2-ethyl-2-isopentylmalonate. In the last step, diethyl 2-ethyl-2-isopentylmalonate undergoes condensation reaction with urea, and gives Amorbarbital.