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EXPERIMENT-2 Synthesis of Benzotriazole From O-Phenylenediamine

This document provides a procedure for synthesizing benzotriazole from o-phenylenediamine. Benzotriazole is prepared by treating o-phenylenediamine with nitrous acid, which is liberated by the reaction of sodium nitrite and acetic acid. This forms a mono-diazonium salt that undergoes spontaneous intramolecular cyclization to produce benzotriazole. The procedure involves dissolving and cooling o-phenylenediamine, then adding sodium nitrite solution which causes the mixture to warm. After filtration and recrystallization, the percentage yield of benzotriazole is calculated and reported.

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Minaz Shah
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7K views3 pages

EXPERIMENT-2 Synthesis of Benzotriazole From O-Phenylenediamine

This document provides a procedure for synthesizing benzotriazole from o-phenylenediamine. Benzotriazole is prepared by treating o-phenylenediamine with nitrous acid, which is liberated by the reaction of sodium nitrite and acetic acid. This forms a mono-diazonium salt that undergoes spontaneous intramolecular cyclization to produce benzotriazole. The procedure involves dissolving and cooling o-phenylenediamine, then adding sodium nitrite solution which causes the mixture to warm. After filtration and recrystallization, the percentage yield of benzotriazole is calculated and reported.

Uploaded by

Minaz Shah
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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AMITY INSTITUTE OF PHARMACY

GWALIOR - MP
(PRACTICAL MANUAL) SECOND YEAR (IV- SEMESTER)
BP406P. MEDICINAL CHEMISTRY – I (Practical-Batch-B)

EXPERIMENT-2: Synthesis of Benzotriazole from o-phenylenediamine


Aim: To synthesize and submit benzotriazole from o-phenylenediamine and report its
percentage yield.
BACKGROUND
Benzotriazole is a bicyclic heterocyclic system consisting of three nitrogen atoms and fused
benzene ring, shows wide range of biological and pharmacological activities.
PRINCIPLE:
Benzotriazole can be prepared by treating o-phenylenediamine with nitrous acid (liberated
during the reaction between sodium nitrite and acetic acid) to form mono-diazonium salt that
follows spontaneous intramolecular cyclization reaction to produce benzotriazole.

Reaction:
Mechanism:

REQUIREMENTS
Chemicals: o-phenylenediamine, Glacial acetic acid, Sodium nitrite.
Apparatus: Beaker, Buchner funnel, Measuring cylinder, Filter paper, glass rod, magnetic stir
PROCEDURE:
1. Dissolve 10.8 g (0.1 mol) of o-phenylenediamine in a mixture of 12 g (11.5 ml, 0.2
mol) of glacial acetic acid and 30 ml of water contained in a 250 ml beaker; slight
warming may be necessary.
2. Cool the clear solution to 15 °C, stir magnetically.
3. Add a solution of 7.5 g (0.11 mol) of sodium nitrite in 15 ml of water in one portion.
The mixture gets warm and reaches a temperature of about 85 °C within 2-3 min and
then becomes cool while the colour of the mixture changes from deep red to pale brown.
4. Continue stirring for 15 min, by which time the temperature will have dropped to 35-
40 °C, and then thoroughly chill in an ice-water bath for 30 min.
5. Collect the product by vacuum filtration of the pale brown solid which separates and
wash with 3x30 ml portions of ice-cold water.
Recrystallisation:
Dissolve the solid in about 130 ml of boiling water, add decolourising charcoal, filter and allow
the filtrate to cool to about 50 °C before adding a few crystals of the synthesized product
(benzotriazole) which have been retained for seeding. Allow the mixture to attain room
temperature slowly (to avoid separation of the material as an oil) and then thoroughly chill in
ice and collect the benzotriazole which separates as pale straw-coloured needles, m.p. 99-100
°C.
Calculation:
Here limiting reagent is o-phenylenediamine; hence yield should be calculated from its amount
taken.
Molecular formula of o-phenylenediamine = C6H8N2
Molecular formula of benzotriazole = C6H5N3
Molecular weight of o-phenylenediamine = 108 g/mole
Molecular weight of benzotriazole = 119 g/mole
Theoretical yield:
108 g o-phenylenediamine forms 119 g benzotriazole
Therefore, 10.8 g o-phenylenediamine will form ………? (X) g benzotriazole
X = (119 × 10.8)/108 = 11.9 g
Theoretical yield = 11.9 g
Practical yield = ————- g
% Yield = (Practical Yield)/(Theoretical Yield) × 100
CONCLUSION
Benzotriazole was synthesized and the percentage yield was found to be………..%
USES:
Used as antifungal, antihypertensive, analgesic etc
REFERENCES
I. Vogel’s Textbook of Practical Organic Chemistry by Brian S. Furniss, Antony J.
Hannaford, Peter W. G. Smith & Austin R. Tatchell; Fifth Edition; Page No. 1163.
II. Practical in organic chemistry, by Hitesh G. Raval, Sunil L. Baldania and Dimal A.
Shah, Nirav Prakashan, Page No. 3

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