So this will be a video in two parts.

For the first reaction we're going to use a small 60 ml capacity beaker equipped with good magnetic stirrin like this.

And now our starting material.

Here we've weighed out 5 grams of glycine powder.

Glycine is an amino acid. In fact the simplest amino acid.

And as you can see its structure is just acetic acid with an amino group on it.

Amino acetic acid.

You can buy it online as an amino acid supplement.

Make sure you're not using the salt of glycine.

Just pure glycine as the free amino acid.

Here's 20 ml of water.

First thing we're going to do is place the water into the beaker and get the stirrin going.

And now we add the glycine powder to the beaker.

It should mostly dissolve.

But it will depend on the temperature of the water.

There's a trick with this reaction which is not to use too much water.

20 ml is enough.

Too much and your yields will suffer badly.

Okay it stirrin away.

What we're going to do with the glycine is acetylate it.

Placing an acetyl group onto the nitrogen to be a mean.

And here's our acetylating agent.

This is 9.5 ml of acetic anhydride.

We've covered off how to make this in a few different videos before.

So check them out for more details.

We've set up a thermometer just to demonstrate the temperature change in the reaction.

But this isn't needed.

It's about 15 degrees to start with.

So now we add the acetic anhydride to the beaker containing our glycine solution.

And now it stirrin vigorously.

If we stop for a second you can see the suspension of acetic anhydride in the water.

Acetic anhydride will react quickly with warm water.

But in cold water that's relatively stable and will react with our glycine before it has a chance to hydrolyze.

Checking the temperature you can see that it's increased by about 10 degrees.

And still climbing a little bit.

So we now set up a small ice bath and cool the reaction mixture back down again.

And soon you can hear the stirrer crunching.

Our product, acetylglycine starts to crystallize out of the mixture as a white precipitate.

Now it's time to be patient.

Let the mixture stir vigorously for a good 20 minutes.

And at the end of this time, chill down in the fridge for 2 hours.

In order to precipitate as much of the product as possible.

Here we go.

A nice white fine precipitate of acetylglycine.

While the mixture is cold, set up for filtration.

Use a very small amount of ice water to wash the beaker and the solid in the filter.

Break up the solid and let it dry on the pump.

Here we go.

A beautiful snow white product.

It's still very slightly damp and for the next reaction we need it to be completely dry.

So we placed it in an oven at 100 degrees C for an hour.

And it turned into a completely dry powder.

Here's the dry product.

5.6 grams of acetylglycine.

Which has hardly any aroma of acetic acid at all.

This is a 72% yield on the starting glycine that we used.

Okay, you're asking, why did we make this?

What can we do with it next?

Well, we're going to try out an interesting reaction called the Erlenmeyer reaction.

Where acetylglycine reacts with an aromatic aldehyde to produce a heterocyclic ring.

Pretty cool, isn't it?

So let's go.

For this next reaction we're going to use a 100 ml flask equipped again with good magnetic stirring.

And we're using a hot plate for careful heating.

Here's our first set of three solid reactants.

Let's go through them.

First we've got 5.6 grams of our dry acetylglycine from the previous reaction.

Next is our aromatic aldehyde.

And we're going to try using vanilline for this.

So we've weighed about 11 grams of vanilline powder here.

And here's our third solid reactant.

This is anhydrous sodium acetate powder.

And we've weighed out 10 grams.

Do know that it's important to use the anhydrous salt and not the hydrate.

Let's get all these solid reactants into the flask.

The acetylglycine.

Vanillin.

The vanillin.

And the anhydrous sodium acetate.

Let's get the stirring switch done and mix all these solids together nicely.

And now for our final reactant.

To make the cyclization happen we also need to use 10 ml of acetic anhydride.

Our solids are now pretty mixed up.

So we add the acetic anhydride to the flask.

The mixture forms a quite solid paste and stirring becomes difficult.

But as you can see the liquid wets the solid quite well in the flask.

Now we're going to switch on the heat.

Gently at first.

Our hot plate setting is 100 degrees C to begin with.

Pretty quickly the mixture loosens up a bit.

And as the mixture warms up it becomes a stirable paste.

And then finally almost liquid again.

Be very careful not to heat the mixture too strongly to begin with.

If you do you can end up with a red colored polymerized mess.

You can also see a slight color change starting to occur.

As the mixture is heated it slowly turns yellow.

At this point we increase the heat just slightly.

We want to get to the point where the entire mixture is almost liquid.

We're using an adapter as a type of air condenser.

Just in case anything distills off.

Pretty soon the mixture becomes a liquid.

A lot more liquid.

And even gets to the point where it looks almost completely liquid.

Apart from a few crystals floating around.

Okay let's look at what's happening in this reaction in more detail.

We won't cover the mechanism in detail as it's too complex.

And there is some debate about what actually happens.

But in the first step.

The acetylglycine cyclysis to form an oxazolone compound called an azelaptone.

This then reacts with the vanilline in the presence of acetic anhydride and the sodium acetate.

Eliminating another molecule of water and forming our target compound.

This process is similar to the perkin reaction.

And if you want to learn about how this actually works then look up details for the perkin reaction mechanism.

Overall.

Two molecules of water are eliminated and the acetic anhydride is converted to acetic acid.

Back to our reaction mixture.

It's now quite fluid.

Once at this stage we kept the heating going for another 45 minutes.

During this time yellow crystals started to form around the flask and in the liquid.

The mixture darkened slightly as you can see.

But never turned a dark orange or red color.

After 45 minutes there's a real build up of crystals in there.

We stop heating at this point.

It is possible with this reaction to go too far and end up destroying the product.

So let's see how we go.

Let the mixture cool and then chill it down in the freezer for a couple of hours.

This is what we got.

A mass of yellow solid in the flask.

It's got a lot of inorganic salts and acetic acid in it still.

So we're going to need to work it up.

We've measured out 40 mils of chloroform.

It might be possible to use dichloromethane as well for this.

But we've not tried it.

Place the chloroform in the flask.

And then stir to gently break up the mass of sticky solid.

Some procedures tell you to add water instead to begin with.

But we found this creates a big mess and using the solvent works better.

Loosen the solids and then get the mixture back on the hot plate and start stirring magnetically.

Heat the mixture gently and you'll soon find that most of the solid goes into solution.

What's left undissolved is mostly sodium acetate.

To make sure we got all the product into solution we heated the mixture up to the boiling point of the chloroform.

About 60 degrees C.

So let's filter the hot mixture now and get rid of the inorganic solids.

Wash the flask and the solids remaining in the filter with a further 10 mils of chloroform.

To make sure that we've got all the product in solution.

After washing you can see the white color of the salts remaining in the filter.

Here's the orange filtrate containing our product.

Get this into the freezer and chill down overnight.

And here's the result the next day.

A mass of yellow crystals have formed in the beaker.

While nice and cold we set up again for filtration and remove the yellow product.

Get it as dry as you can on the pump and then place back into the beaker.

Our product still has some acetic acid in it.

So to remove this we need to do a final wash.

We're going to do this using petroleum ether.

We found that the yellow crystals do have a tendency to turn back into an oil in the presence of water and regular diethyl ether.

So the solvent choice here is important.

It's a tricky substance to crystallize and we found that evaporating down solutions of the product in DCM or other solvents left acetic the oil which was then very difficult to crystallize.

So now we filter and dry the product.

Here we go.

6.2 grams of our product of aniline substituted for benzylitone to methyl oxazole 5-one.

That wasn't hard to pronounce at all.

And this is a 55% yield on our starting acetylglycine.

Which is great.

It's a really beautiful intense yellow color.

It means anything it touches bright yellow.

One trick to help clean up is to make up a warm solution of sodium hydroxide in water.

In strongly alkaline solution the product dissolves and is actually hydrolyzed forming a bright red colored solution.

The hydrolysis breaks the oxazolone ring forming the cinnamic acid derivative as you can see here.

And what's very interesting is that the oxazolone.

It's the proton reduction of the carbon to carbon double bond.

This then forms another amino acid.

This time the substituted analog of tyrosine.

A phenethylamine derivative.

If you compare the structures.

It's actually very similar to the dopamine molecule.

A very important neurotransmitter occurring naturally in your nervous system.

So it's an interesting product and we might come back to it and do some follow up reactions in a future video.

That's all for now though.

Thanks for watching and stay tuned.