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Medicinal Chemistry Practicals: Semester IV

This document provides information about the synthesis of benzocaine from para-amino benzoic acid (PABA) and ethanol. It discusses that the esterification reaction proceeds slowly without a catalyst. Adding a small amount of sulfuric acid as a catalyst enhances the rate of the forward reaction by displacing the equilibrium towards the product. The mechanism involves the sulfuric acid catalyzed reaction of PABA and ethanol to form the benzocaine sulfate salt. Sodium carbonate is then added to release the free ethyl-4-amino benzoate product while avoiding conditions that could hydrolyze the ester. The procedure, mole table and expected results are also outlined.

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115 views

Medicinal Chemistry Practicals: Semester IV

This document provides information about the synthesis of benzocaine from para-amino benzoic acid (PABA) and ethanol. It discusses that the esterification reaction proceeds slowly without a catalyst. Adding a small amount of sulfuric acid as a catalyst enhances the rate of the forward reaction by displacing the equilibrium towards the product. The mechanism involves the sulfuric acid catalyzed reaction of PABA and ethanol to form the benzocaine sulfate salt. Sodium carbonate is then added to release the free ethyl-4-amino benzoate product while avoiding conditions that could hydrolyze the ester. The procedure, mole table and expected results are also outlined.

Uploaded by

Gaurav Mudadu
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PPTX, PDF, TXT or read online on Scribd
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Medicinal Chemistry

Practicals
Semester IV
Syllabus
Syllabus
Benzocaine

• Local anesthetic agent


• Indicated to treat a variety of pain-related conditions. It may be used for:
• Local anesthesia of oral and pharyngeal mucous membranes (sore throat,
cold sores, mouth ulcers, toothache, sore gums, denture irritation)
• Otic pain (earache)
• Surgical or procedural local anesthesia
• Functional groups
• Ester
• Aromatic amine
Synthesis
• Benzocaine can be synthesized from Para Amino Benzoic Acid (PABA) and ethanol

• The interaction between a carboxylic acid and an alcohol is a reversible process


and proceeds very slowly. Equilibrium is only attained after refluxing for several
days.
Synthesis
• Benzocaine can be synthesized from Para Amino Benzoic Acid (PABA) and ethanol

• If about 3% of either conc. sulphuric acid or a dry hydrogen chloride is added to a


mixture, the same point of equilibrium can be reached after few hours.
Rate of forward reaction is enhanced
• Rate of forward reaction is enhanced by -
• The equilibrium may be displaced towards the right by using
sulphuric acid as a catalyst.
• The equilibrium may be displaced towards formation of the ester
by the use of excess of any of the reactants. It is frequently
convenient to use an excess of the acid, but if the acid is expensive
a large excess of alcohol can be employed.
Mechanism
NH3+

Sod carbonate

• Since sulfuric acid is used to catalyse the esterification, the


benzocaine formed exists as sulphate salt.
• To release free ethyl-4-amino benzoate, an alkali like sodium
carbonate is added.
• Excess of sodium carbonate if added can cause a base
catalyzed hydrolysis of ester. So it should be added just to
make the pH neutral.
• Use of strong bases like NaOH should be avoided as they may
hydrolyse the ester formed.
Procedure
Mole table
Theoretical yield

Stoichiometric ratio 1 mole PABA gives 1 mole Benzocaine


Mol formula C7H7NO2 C9H11O2N
Mol weight 137 165

?
Result
Structure of the product  

IUPAC name of the product  

Appearance of the product  

Practical yield  

Percent yield  

Melting point  

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