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Synthesis of Benzotriazole from
o- Phynylenediamine
MEDICINAL CHEMISTRY- I
-Pratik Terse 1
Aim:
• To prepare and submit Benzotriazole from o-
phenylenediamine/
• To perform synthesis of Benzotriazole.
What is Benzotriazole?
• Benzotriazole (BTA) is a heterocyclic compound containing
three nitrogen atoms, with the chemical formula C6H5N3.
• This aromatic compound is colorless and polar and can be
used in various fields..
Synthesis of Benzotriazole from
o- Phynylenediamine
-Pratik Terse 2
Synthesis of Benzotriazole from
o- Phynylenediamine
-Pratik Terse 3
Properties of Benzotriazole:
• Solubility: It is soluble in water
• Melting point: 99-100℃
• Molecular formula: C6H5N3
• Molecular Weight: 119.1 g/mol
Uses of Benzotriazole:
• Antifungal, Antihypertensive, Analgesic drug
• It is also an effective corrosion inhibitor for copper and
its alloy.
Synthesis of Benzotriazole from
o- Phynylenediamine
• Apparatus:
Round bottom flask, beaker,
condenser assembly, Water
bath, Magnetic stirrer.
• Chemicals:
o-Phenylenediamine, Sodium
nitrate, Glacial acetic acid,
Distilled water
REQUIREMENTS:
-Pratik Terse 4
Synthesis of Benzotriazole from
o- Phynylenediamine
-Pratik Terse 5
Magnetic Stirrer:
• A magnetic stirrer or magnetic mixer is a laboratory device that
employs a rotating magnetic field to cause a stir bar (or bead)
immersed in a liquid to spin very quickly, thus stirring it.
Synthesis of Benzotriazole from
o- Phynylenediamine
-Pratik Terse 6
Precursor for the practical:
O- Phenylenediamine
• Its is an organic aromatic diamine
• Mol. Formula: C6H8N2
• Mol. Weight: 108 g/mol
Sodium nitrate:
• Mol. Formula: NaNO2
• Mol. Weight: 68.9 g/mol
• White ro slightly yellowish
• Soluble in water
Synthesis of Benzotriazole from
o- Phynylenediamine
-Pratik Terse 7
Glacial Acetic Acid:
• Mol Formula: CH3COOH
• It is polar aromatic solvent
• Used as a catalyst
Synthesis of Benzotriazole from
o- Phynylenediamine
-Pratik Terse 8
Theory:
• Benzotriazole is synthesized by reaction of o-Phenylenediamine,
Sodium nitrate and Acetic acid.
• The conversion proceeds by diazotization of one of the amine
group.
Principal:
• Benzotriazole can be prepared by treating o-Phenylenediamine
with nitrous acid, which is liberated during the reaction of nitrite
and acetic acid to form mono- diazonium salt that follows
spontaneous intramolecular cyclization reaction to form
Benzotriazole.
Synthesis of Benzotriazole from
o- Phynylenediamine
-Pratik Terse 9
Synthesis of Benzotriazole from
o- Phynylenediamine
-Pratik Terse 10
Procedun:
• Dissolve 10.8 g (0.1 mol) 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.
• Cool the clear solution to 15℃ stir magnetically and then add a solution of 7.5 g (0.1-1 mol) of
sodium nitrite in I5 ml of water in one portion,
• The reaction mixture becomes warm and within 2-3 minutes reaches a temperature of 85℃
and then begins to cool while the colour changes from deep red to pale brown.
• Continue stirring for 15 minutes, by which temperature will have dropped to 35-40℃ and then
thoroughly chill in an ice-water bath for 30 min.
• Collect by vacuum filtration and wash with three 30 ml portions of ice-cold water.
• Dissolve the solid in about 130 ml of boiling water, add decolorizing charcoal, filter and allow
the filtrate to cool to about 50℃ before adding a few crystals of the crude benzotriazole which
have been retained for seeding.
• Allow the mixture to attain room temperature slowly (to avoid separation of the material as oil).
• Then thoroughly chill in ice and collect the benzotriazole which separates as pale yellow straw-
coloured needles, M.P. 99-100℃.
• A second crop may be obtained by concentrating the filtrate. The yield is about 8 g (65%)
Synthesis of Benzotriazole from
o- Phynylenediamine
-Pratik Terse 11
Calculations:
• Mol. wt. of o- Phenylenediamine=
• Mol. wt. of Benzotriazole=
• Theoretical yield:
108g of o- Phenylenediamine gives 119.1 g of
Benzotriazole
Therefore:
Synthesis of Benzotriazole from
o- Phynylenediamine
-Pratik Terse 12
• Practical yield: Suppose you get 8 g
• % Practical yield:
𝑃𝑟𝑎𝑐𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
𝑇ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
× 100
• % Practical yield:
• Result: The practical of benzotriazole was found to
be ____g and the % practical was _____% and the
melting point was found to be____℃
Synthesis of Benzotriazole from
o- Phynylenediamine
-Pratik Terse 13
Synthesis of Benzotriazole
• Molecular formula: C6H5N3
• Molecular weight: 119.1 g/mol
• Theoretical yield: 11.91 g
• Practical yield: 8 g
• % Practical yield: 67%
• Melting point: 100
Remember…
Safety First!
Thank You!!!
-Pratik Terse 14

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Synthesis of Benzotriazole from o- Phynylenediamine.pptx

  • 1. Synthesis of Benzotriazole from o- Phynylenediamine MEDICINAL CHEMISTRY- I -Pratik Terse 1
  • 2. Aim: • To prepare and submit Benzotriazole from o- phenylenediamine/ • To perform synthesis of Benzotriazole. What is Benzotriazole? • Benzotriazole (BTA) is a heterocyclic compound containing three nitrogen atoms, with the chemical formula C6H5N3. • This aromatic compound is colorless and polar and can be used in various fields.. Synthesis of Benzotriazole from o- Phynylenediamine -Pratik Terse 2
  • 3. Synthesis of Benzotriazole from o- Phynylenediamine -Pratik Terse 3 Properties of Benzotriazole: • Solubility: It is soluble in water • Melting point: 99-100℃ • Molecular formula: C6H5N3 • Molecular Weight: 119.1 g/mol Uses of Benzotriazole: • Antifungal, Antihypertensive, Analgesic drug • It is also an effective corrosion inhibitor for copper and its alloy.
  • 4. Synthesis of Benzotriazole from o- Phynylenediamine • Apparatus: Round bottom flask, beaker, condenser assembly, Water bath, Magnetic stirrer. • Chemicals: o-Phenylenediamine, Sodium nitrate, Glacial acetic acid, Distilled water REQUIREMENTS: -Pratik Terse 4
  • 5. Synthesis of Benzotriazole from o- Phynylenediamine -Pratik Terse 5 Magnetic Stirrer: • A magnetic stirrer or magnetic mixer is a laboratory device that employs a rotating magnetic field to cause a stir bar (or bead) immersed in a liquid to spin very quickly, thus stirring it.
  • 6. Synthesis of Benzotriazole from o- Phynylenediamine -Pratik Terse 6 Precursor for the practical: O- Phenylenediamine • Its is an organic aromatic diamine • Mol. Formula: C6H8N2 • Mol. Weight: 108 g/mol Sodium nitrate: • Mol. Formula: NaNO2 • Mol. Weight: 68.9 g/mol • White ro slightly yellowish • Soluble in water
  • 7. Synthesis of Benzotriazole from o- Phynylenediamine -Pratik Terse 7 Glacial Acetic Acid: • Mol Formula: CH3COOH • It is polar aromatic solvent • Used as a catalyst
  • 8. Synthesis of Benzotriazole from o- Phynylenediamine -Pratik Terse 8 Theory: • Benzotriazole is synthesized by reaction of o-Phenylenediamine, Sodium nitrate and Acetic acid. • The conversion proceeds by diazotization of one of the amine group. Principal: • Benzotriazole can be prepared by treating o-Phenylenediamine with nitrous acid, which is liberated during the reaction of nitrite and acetic acid to form mono- diazonium salt that follows spontaneous intramolecular cyclization reaction to form Benzotriazole.
  • 9. Synthesis of Benzotriazole from o- Phynylenediamine -Pratik Terse 9
  • 10. Synthesis of Benzotriazole from o- Phynylenediamine -Pratik Terse 10 Procedun: • Dissolve 10.8 g (0.1 mol) 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. • Cool the clear solution to 15℃ stir magnetically and then add a solution of 7.5 g (0.1-1 mol) of sodium nitrite in I5 ml of water in one portion, • The reaction mixture becomes warm and within 2-3 minutes reaches a temperature of 85℃ and then begins to cool while the colour changes from deep red to pale brown. • Continue stirring for 15 minutes, by which temperature will have dropped to 35-40℃ and then thoroughly chill in an ice-water bath for 30 min. • Collect by vacuum filtration and wash with three 30 ml portions of ice-cold water. • Dissolve the solid in about 130 ml of boiling water, add decolorizing charcoal, filter and allow the filtrate to cool to about 50℃ before adding a few crystals of the crude benzotriazole which have been retained for seeding. • Allow the mixture to attain room temperature slowly (to avoid separation of the material as oil). • Then thoroughly chill in ice and collect the benzotriazole which separates as pale yellow straw- coloured needles, M.P. 99-100℃. • A second crop may be obtained by concentrating the filtrate. The yield is about 8 g (65%)
  • 11. Synthesis of Benzotriazole from o- Phynylenediamine -Pratik Terse 11 Calculations: • Mol. wt. of o- Phenylenediamine= • Mol. wt. of Benzotriazole= • Theoretical yield: 108g of o- Phenylenediamine gives 119.1 g of Benzotriazole Therefore:
  • 12. Synthesis of Benzotriazole from o- Phynylenediamine -Pratik Terse 12 • Practical yield: Suppose you get 8 g • % Practical yield: 𝑃𝑟𝑎𝑐𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑 𝑇ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑 × 100 • % Practical yield: • Result: The practical of benzotriazole was found to be ____g and the % practical was _____% and the melting point was found to be____℃
  • 13. Synthesis of Benzotriazole from o- Phynylenediamine -Pratik Terse 13 Synthesis of Benzotriazole • Molecular formula: C6H5N3 • Molecular weight: 119.1 g/mol • Theoretical yield: 11.91 g • Practical yield: 8 g • % Practical yield: 67% • Melting point: 100