16/11/2021

OUR LADY OF FATIMA UNIVERSITY

COLLEGE OF PHARMACY UNIT OUTCOMES
At the end of this module, the • Checklist
students are expected to: – Read course outcomes
EXPERIMENT 6 • the student should be able – Read course guide
SYNTHESIS OF ACETANILIDE to know how to synthesize prior to class
attendance
acetanilide and to
Post-Laboratory Discussion determine its identity – Proactively participate
through chemical tests in discussions
PHARMACEUTICAL AND MEDICINAL
– Watch videos related
ORGANIC CHEMISTRY to the topic
– Answer and submit
course unit tasks

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PMOC311 LAB

Acetylsalicylic Acid Acetanilide

• N-phenylacetamide • White leaflets or
• Acetanil flakes, odorless
• 2-acetanilide • Melting point: 114-
• Acetic acid anilide 116°C
• Ethananilide • Boiling point: 304°C
• Acetylaniline • Specific gravity:1.219
• Acetylaminobenzene • Solubility: soluble in
• Antifebrin hot water
• N-acetylaniline
• Acetaminobenzene

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PMOC311 LAB OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PMOC311 LAB

Purification of Acetanilide by
Acetanilide Synthesis Crystallization Method from Water
• Recrystallization/Crystallization
– Purification procedure that requires solubility of the
impure solid in a heated solution and crystallization
of the solid upon colling

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PMOC311 LAB OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PMOC311 LAB

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Chemical Tests Chemical Tests

• Hydrolysis of Acetanilide
+ H2O +
• Bromination
– The bromination of 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.
H+ +

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PMOC311 LAB OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PMOC311 LAB

How does the structure of Amine

Acetanilide
differ from that of amide?
• N-acetyl aniline
• Phenylacetanilide
• AMINE AMIDE
RNH2 RC=ONH2

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PMOC311 LAB

Acetaminophen Aspirin Acetaminophen Naproxen

• N-acetyl-p- • Acetylsalicylic acid • 2-(4-isobutylphenyl) • (+)-6-methoxy-a-
aminophenol/ propionic acid methyl-2-
• 4-hydroxyacetanilide naphthaleneacetic
acid

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PMOC311 LAB OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PMOC311 LAB

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Ketoprofen
• 3-benzoyl-a-methylbenzeneacetic acid
• m-benzoylhydratropic acid

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PMOC311 LAB OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PMOC311 LAB