Synthesis ACETANILIDE

● N-phenylacetamide

● Acetanil

● 2-Acetanilide

● Acetic acid anilide

● CAN

● Ethananilide

● Acetylaniline

● Acetylaminobenzene

● Antifebrin

● N-Acetylaniline

● Acetaminobenzene

ACETANILIDE aka

Amide

derivative of carboxylic acid that is added

with an amino group

White leaflets or flakes

ACETANILIDE appearance

odorless

ACETANILIDE Odor

114-116°C

ACETANILIDE MP

304 °C

ACETANILIDE BP

1.219

ACETANILIDE SG

Soluble in hot water

ACETANILIDE solubility

Causes severe irritation in the mucous membrane

Pungent and corrosive odor

Why need to ~> Fumehood

2mL acetic anhydride

2mL Aniline (C6H5NH2)

2mL Glacial acetic acid

Reagent used

Flat-bottomed Florence Flask

Flask used

Waterbath → +20mL ice cold H2O

After adding the reagents.

Acetanilide + HCL

Acetyl Chloride

Acetanilide + Acetic acid

Acetic anhydride

Recrystallization (Crystallization

is a purification procedure, which requires

solubility of the impure solid in a heated

solution and crystallization of the solid upon

cooling.

Acetanilide

Paracetamol parent comp.

Paracetamol

Hydroxylated metabolite of Acetanilide

para-nitroaniline (C6H62O2)

Hydrolysis of Acetanilide

→ Acetyl group can then be removed by

acid-catalyzed hydrolysis to yield

Bromination

acetanilide forms a

mono-brominated product as the major product of the

reaction, while bromination of aniline forms a

tri-brominated product as the major product.

mono-brominated product (para position 1,4)

acetanilide forms a (major product)

tri-brominated product (2,4,6)

aniline forms a (major product)

Acetaminophen

Acetanilide –(Aromatic hydroxylation)-->

Aniline

Acetanilide –(Amide hydrolysis)-->

Phenylhydroxylamine

Aniline

–(n-hydroxylation)-->

Brominated Acetanilide (para bromo acetanilide)

Major product

peroxides and

stabilizer for cellulose ester varnishes.

Industrial Uses

- Acetanilide is used as

intermediate for the synthesis of

rubber accelerators, dyes, dye intermediate and

camphor.

Acetanilide is used as an

Phenylhydroxylamine

Responsible for the toxicity of Acetanilide causing methemoglobinemia

Phenylacetamide

structure shows analgesic and

antipyretic effects. But acetanilide is not used directly

for this application due to causing

methemoglobinemia (the presence of excessive

methemoglobin, which does not function reversibly as

an oxygen carrier in the blood).

N-acetyl aniline and of

phenylacetanilide. It is neutral to litmus paper.

The chemical Acetanilide is

Amide contains carbonyl group

difference between amine and amide

Acetaminophen,

N-acetyl-para-aminophenol

4-hydroxyacetanilide

Acetaminophen aka

Inhibits Cox3 in the brain

Acetaminophen MOA

Acetylsalicylic acid

Aspirin aka

Inhibits COX

Aspirin MOA

Thromboxane

Stimulates platelet aggregation

325mg - 650mg every 6hrs

Aspirin dose for antipyretic and analgesic

75mg - 325mg every day to prevent 2nd heart attack

Aspirin dose for antiplatelet

Arachidonic acid

Precursor of prostanoids

Arachidonic acid

Cosanoid derived from 20C unsaturated FA

Leukotrienes

Causes bronchoconstriction

Corticosteroids

Inhibits phospholipase A2

Zileuton

Lipoxygenase inhibited by the drug which is used for Asthma

Zafirlukast

Inhibit the interaction of leukotrienes to the receptor

Aspirin (Non steroidal anti inflammatory drug)

Cylooxygenase inhibited by what drug

Ulcer

Bleeding disorder

Asthma

Gout

Children with viral infections causes Reye’s syndrome

Contraindication of Aspirin

2-(4-isobutylphenyl)

propionic acid

Ibuprofen aka

6-methoxy-a-methyl-2

naphthaleneacetic acid

Naproxen aka

Naproxen

The only NSAID that is marketed as single enantiomer

3-benzoyl-a-methylbenzeneacetic acid/

m-benzoylhydratropic acid

Ketoprofen aka

methemoglobinemia and

jaundice.

Acetanilide is used as analgesic and anti-pyretic agent

that in high doses can cause

White precipitate at

the upper and lower layer while clear

appearance at the middle layer

Acetanilide- (+) Result

yellow slimy substance at

the middle junction

Aniline- (+) Result:

Acetaminophen

Aspirin

Ibuprofen

Naproxen

Ketoprofen