I. Chemical reactions: Consultation/reference to literature should be considered as the use of well documented chemical reactions for the synthetic route will lead to higher yields and less impurities. II. Catalysts: The use of a catalyst can be an advantage however it may generate waste that requires disposal. Some manufacturers develop a catalyst for a specific reaction however this may be time consuming. III. Starting materials availability: Availability of bulk chemicals that are cost effective must also be considered IV. Environmental factors: Safe containment of solvents reagents and waste disposal must also be considered. V. Number of steps: A synthetic route which requires fewer steps results in lower utilization time of equipment …show more content…
Ibuprofen: Part B. Figure 1. Structural features of Ibuprofen Ibuprofen has two functional groups; Carboxyl group (COOH) and an aromatic group (Benzene ring) the chemical formula for ibuprofen is C13H18O2. Part C. Ibuprofen consists of covalently-bonded carbon, hydrogen, and oxygen atoms. Two CH3 molecules are single-bonded to a CH molecule. The CH molecule is bonded to a carbon atom that forms a 6-sided ring of carbon atoms. Another CH molecule is single-bonded to a carbon atom on the other side of the ring. There are 3 double bonds inside the rings between carbon atoms. On the right, another CH3 molecule and a COOH molecule are both single bonded to the CH molecule. The following is the synthetic chemistry routes for synthesizing Ibuprofen. Step 1: Isobutyl benzene is combined with propionyl chloride through Friedel-Crafts acylation to form 1-(4-Isobutyl-phenyl)-propan-1-one. Step 2: 1-(4-Isobutyl-phenyl)-propan-1-one is converted to methyl ibuprofen through treatment with iodine and trimethyl orthoformate via aryl migration. Step 3: Methyl ibuprofen is hydrolyzed to ibuprofen by potassium …show more content…
Step 2: Diethyl 2, 4-dichloro-5-fluorobenzoylmalonate is partially hydrolyzed and decarboxylated with tosylic acid to yield ethyl 2, 4-dichoro–5 fluorobenzoylacetate (17). Step 3: Ethyl 2, 4-dichoro–5 fluorobenzene undergoes condensation (Dieckman like) with ethyl orthoformate which is carried out in refluxing acetic anhydride and results in ethyl 2(2-4-dichloro-5-fluorobenzoyl)-3-ethoxyacrylate. (18). Step 4: This is treated with cyclopropyl amine in ethanol to give ethyl 2-(2, 4-dichloro-5-fluoronenzoyl)-3-cyclopropylaminoacrylate.This results in removal (Michael addition) of the ethoxy group resulting in the enamine (19). Step 5: An intramolecular SNAr reaction of the enamine takes place resulting in a cyclised quinolone (20). This is formed in basic conditions using a base such as NaH or KH. Step 6: The ethyl ester on (20) is hydrolysed using concentrated sulphuric acid in a refluxing 1:1 acetic acid/water mixture. Step 7: SNAr displacement takes place of 6-fluro-7-chloroquinlone (21) with piperzine to yield
This ester in this experiment is isopentyl acetate formed from acetic acid and isopentyl alcohol. The reaction is catalyzed by hydrochloric acid, a Fisher esterification process, (McMurry, p780-781) but the catalyst affects only the rate of reaction, and not the extent of reaction. The desired product accumulates only if the equilibrium constant is favorable.
The invention of aspirin, a medical-breakthrough, mainly belongs to the knowledge of chemistry. In order to study how aspirin actually work and its possible side-effect, pharmacology knowledge is also needed.
Step one is known as the preparation of 2,6-dimethylaniline. The preparation of 2,6-dimethylaniline is a reduction reaction. Step two is the preparation of α-chloro-2,6-dimethylacetanilide. This second step is an acylation reaction. The final step of the synthesis is the preparation of lidocaine. The preparation of lidocaine reaction is nucleophilic substitution.
In this lab 2-methyl-butyn-2-ol is hydrated to 3-hydroxy-3-methyl-2-butanone. This process was preformed by using a strong acid which created an enol, and then the enol tautomerized. Due to this being a terminal alkyne, only one product will be formed. Techniques such as simple distillation, reflux, and gravity filtration were used to produce and separate the product from the mixture that it was in. When performing this lab using only one equivalent of alkyne produced a low percent of 1%. The low yield is a result of using one equivalent instead of two.
Reacting 1-butanol produced 2-trans-butene as the major product. 1-butanol produces three different products instead of the predicted one because of carbocation rearrangement. Because of the presence of a strong acid this reaction will undergo E1 Saytzeff, which produces the more substituted
The components of an analgesic will be determined by noting the separation between the solid and liquid (or mobile) phases and comparing it to these predicted reference values.
The next type of spectra to look at is Carbon NMR. In Carbon NMR a spectrum is produced that has peaks for each unique carbon in the molecule. Carbon NMR is possible because radio waves are shot through a sample already aligned on a very large magnet and the nuclei of the atoms switch to a higher energy state. It requires different wavelengths to flip different carbons. The locations of the peaks on the spectrum shows what type of functional groups the carbons are part of. Figure 6 shows the Carbon NMR for ibuprofen. In the figure there is a drawing of ibuprofen with the unique carbons numbered. These numbers align to the spectra underneath and the information given in purple. Anywhere from 10-60ppm are alkanes. That means there should have
Baran and his team showed that they could use their new method to directly append a strained-ring molecule favored by pharmaceutical chemists—propellane, so-called because its structure resembles a propeller—to existing larger drug molecules. ‘We can make that five-carbon ring structure of propellane click onto a wide range of drug molecules of a type known as secondary amines—we call that a propellerization reaction,’ said Lopchuck.”
Background Information Aspirin is an analgesic (pain relieving) and an antipyretic drug (a drug that lowers body temperature). The main constituent of aspirin is 2 - ethanoythydroxybenzoic acid, also known as acetylsalicyclic acid (shown below right). It was originally made from just salicylic acid (which is found in the bark of a willow tree) when used by the Ancient Greeks to counter fever and pain, but its bitterness and tendency to irritate the stomach caused problems. These were resolved by the German chemist Felix Hoffman, who made the acetyl derivative of salicylic acid in the
The Royal Society of Chemistry. (2013). The Discovery of Ibuprofen. Retrieved December, 27, 2013, from http://www.rsc.org/learn-chemistry/resources/chemistry-in-your-cupboard/nurofen/7.
The only anti-inflammatory drug for over a half a century was Aspirin. Unfortunately, Aspirin causes many side effects when taken in large doses such as ulcers and bleeding in the intestines. Experts knew they had to discover another remedy to help pain sufferers. A medicine alternative called Paracetamol was discovered, but did nothing to take away pain. In 1948, Cortisone was discovered. It was considered a miracle until side effects developed from the drug. In 1980, Ibuprofen went over the counter and has become the most well-known anti-inflammatory. Pain relief has come along way through the years. It has not always been as easy as it is now to get rid of pain. Many people had to suffer because of having no solid pain relieving methods.
The production of synthetic detergents are an example of a standard chemical approach. If a useful substance has some undesirable properties an attempt is made to make a near copy synthetically which will perform better.
It is important to have clean and long-lasting environment because today the world faces increasing environmental issues, such as pollution. This cannot happen only by decreasing the amount of people's waste or using less energy. Thinking deeply about developing protection processes is also important as well as realizing how these issues affect people's life in present and future. Therefore, chemical engineers take environmental problems into account to decrease pollution. Rattan (2014) explained that beside other problems, saving environment, controlling toxic materials pushes chemical engineers to take into consideration any areas related to modern ecological safety in community. To illustrate, today chemical engineers oversee and improve safe production processes through controlling pathways of reaction and see if it produces pollution or not. Moreover, reducing, treating and safely disposing unused products is another way chemical engineering has contributed to protecting the
2). The cycle is broken into eight consecutive stages (Table 1). The first step initiating the cycle involves acetyl CoA reacting with oxaloacetate to first produce citryl CoA and then citrate from further hydrolysis. In the second step, citrate is isomerised into isocitrate. This is achieved through a dehydration and hydration step with cis-Aconistase produced as an intermediate and the aconitase catalysing the overall reaction. The third step involves isocitrate undergoing decarboxylation and oxidation reactions to form alpha-ketoglutarate (Berg J.M et al., 2015). In step four, a second decarboxylation oxidation reaction occurs to form succinyl CoA from alpha-ketoglutarate. Step five involves splitting succinyl CoA to produce succinate and CoA. In step six, succinate is oxidised to fumurate and FADH2 is formed simultaneously (Ness B., 2017). The penultimate step involves fumurate being converted to malate. In the affixing step of the citric acid cycle, malate is oxidised to form oxaloacetate, enabling a cycle to be established (Berg J.M et al., 2015).