Synthesis of Hydantoin & Its Derivatives

Instructor: Korry Barnes

Korry has a Ph.D. in organic chemistry and teaches college chemistry courses.

The focus of this lesson will be on a heterocyclic organic compound known as hydantoin. Our primary points of discussion will be on its structure, synthesis, and important derivatives.

Hydantoin Day in Organic Lecture

It's that day of the week again and Justin is heading in to his organic chemistry lecture for the next couple of hours. Justin is majoring in biomedical sciences, with hopes of gaining entry into medical school one day. He really has been enjoying organic chemistry, as he believes a good foundational knowledge of this intricate subject will serve him well as a medical professional one day.

Currently, Justin's class has been studying amide compounds, and today they are going to be talking about a specific amide, or O = C-NH2, known as hydantoin. Their professor is going to be talking with them about hydantoin's structure, how it's made synthetically, and some of the more important derivatives that have real-world applications. Let's listen in and learn about hydantoin along with Justin and the rest of the class!

Structure of Hydantoin

Hydantoin is a heterocyclic amide (amide is the functional group), which means structurally it contains a ring system in which at least one of the ring-atoms is not carbon. Since it is an amide, it contains a carbonyl group (carbon-oxygen double bond) connected to a nitrogen atom. Hydantoin actually could be thought of as a di-amide because it contains two amide functional groups inside the ring.

Structure of hydantoin

Notice in the structure that the ring size is five atoms, with three of the atoms composing the ring being carbon and two of them being nitrogen. Also notice the carbon-oxygen double bonds connected to the nitrogen atoms. Those are the amide functional groups.

Synthesis of Hydantoin

Hydantoins arent typically isolated from natural sources like plants, mammals, or microorganisms, so they have to be made synthetically in the lab setting. Hydantoins have been known for quite a while, with synthetic reports dating back to the late 1800's. An example is a method reported by Friedrich Urech in which he was able to make 5-methylhydantoin by reacting alanine sulfate (an amino acid in salt-form) with potassium cyanate (KOCN). This reaction can be general, and works with a variety of amino acids, which is why we use the 'R' group on the amino acid structure.

Urech hydantoin synthesis involving an amino acid and potassium cyanate

Hans Theodor Bucherer was able to demonstrate that Urech was not the only one who could make hydantoins. In what's called the Bucherer-Bergs reaction, a carbonyl compound (either an aldehyde or ketone) is reacted with ammonium carbonate and potassium cyanide to make hydantoins in good synthetic yields. This reaction is helpful because it doesn't rely on the use of amino acids but rather carbonyl compounds, which are widely abundant, commercially available, and relatively cheap.

Bucherer-Bergs reaction scheme in which a carbonyl compound reacts with ammonium carbonate and potassium cyanate to make a hydantoin

Derivatives of Hydantoin

Now that we know what hydantoin looks like in terms of its structure and how it's made, let's look at some of the more important derivatives. When we're talking about derivatives of hydantoin, we're talking about complex molecules that contain the hydantoin structure as part of the larger molecule. Phenytoin is an FDA-approved drug that contains hydantoin, and is primarily used for treating patients with seizures. Phenytoin actually is an anti-seizure medication, which means it helps prevent them.

Structure of phenytoin, an anti-seizure medication

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