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Synthesis of benzotriazole from o-phenylenediamine

BP406P Medicinal Chemistry I Practical


AIM:

To synthesize and submit benzotriazole from o-phenylene diamine and report its percentage yield.

REFERENCE:

  1. Practical medicinal chemistry by Dr. Devala Rao, page no:35.
  2. Comprehensive practical organic chemistry by V.K.Ahluwalia and Renu Aggarval, page no:121.

CHEMICAL REQUIREMENTS:

o-phenylenediamine, glacial acetic acid, sodium nitrite

PRINCIPLE:

The sodium nitrite reacts with glacial acetic acid and liberates nitrous acid. The o-phenylene diamine reacts with nitrous acid and produces a diazonium ion. When the structure and stereochemistry of diazonium ion are stable, intramolecular nitrogen coupling occurs and forms benzotriazole directly.

CALCULATIONS

The molecular weight of o-phenylene diamine = Molecular weight of benzotriazole =

—- g of o-phenylene diamine gives —- g of benzotriazole 1g of o-phenylene diamine                    =

=

—- g of o-phenylene diamine   =

Theoretical yield                       =

Practical yield                           =

Percentage yield                       =

PROCEDURE:

Dissolve 1.3g of o-phenylenediamine in a mixture of 1.5ml of glacial acetic acid and 5ml water in a beaker. Stir until the solid dissolves, warm gently if necessary. Cool the solution to 150C. Stir well and add a solution of 2g of sodium nitrite in 2ml water. Reaction mixture become warm within 2-3 minutes and reaches a temperature of about 850C and then begins to cool. Colour changes from deep red to pale brown. Continue stirring for 15 minutes till the temperature fall about 35-400C. Thoroughly chill in ice bath for 30 minutes. Filter the product and wash with cold water.

USE:

Used in bulk drug industry as an important intermediate compound.

It is the basic nucleus present in anthelmintic drugs like mebendazole, thiabendazole etc.

REPORT:

Benzotriazole was prepared and submitted. The percentage yield was found to be ———


Second Year B Pharm Notes, Syllabus, Books, PDF Subjectwise/Topicwise

S Y B Pharm Sem IIIS Y B Pharm Sem IV
BP301T Pharmaceutical Organic Chemistry II TheoryBP401T Pharmaceutical Organic Chemistry III Theory
BP302T Physical Pharmaceutics I TheoryBP402T Medicinal Chemistry I Theory
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BP305P Pharmaceutical Organic Chemistry II Practical BP405T Pharmacognosy I Theory
BP306P Physical Pharmaceutics I PracticalBP406P Medicinal Chemistry I Practical
BP307P Pharmaceutical Microbiology PracticalBP407P Physical Pharmaceutics II Practical
BP308P Pharmaceutical Engineering PracticalBP408P Pharmacology I Practical
BP409P Pharmacognosy I Practical

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