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Synthesis of Phenothiazine
from Diphenylamine.
1
Synthesis of Phenothiazine from
Diphenylamine.
Aim:
• To prepare and submit Phenothiazine from Diphenylamine.
Requirements:
• Apparatus: Round bottom flask, reflux condenser, water bath, oil bath.
• Chemicals: Diphenylamine, Iodine, Ethanol, Charcoal, Sulphur.
Theory:
• Diphenylamine when treated with Sulphur undergo fusion reaction in the presence of
iodine to give Phenothiazine a tricyclic compound used as an antihistamine
engagement.
-Pratik Terse
2
Synthesis of Phenothiazine from
Diphenylamine.
Diphenylamine:
• Molecular formula of Diphenylamine: C12H11N
• Molecular wt. of Diphenylamine: 169 g/mol
Phenothiazine:
• Molecular formula of Phenothiazine: C12H9NS
• Molecular wt. of Phenothiazine : 199 g/mol
-Pratik Terse
3
Synthesis of Phenothiazine from
Diphenylamine.
Procedure.
• In a round bottom flask fitted with reflux condenser place 6.4 grams of
Suphur, 16.8 gram Diphenylamine, and 300 mg Iodine.
• Reflux the mixture on an oil bath at 190 to 200℃ for 30 to 40 minutes.
• Cool and grind the residue mass in which 5 ml of ethanol and pinch of
animal charcoal is added and heated it until solid mass dissolves.
• Filter the solution while hot and cool in ice bath.
• Filter the reaction mixture and obtain as yellow crystals of phenothiazine.
• Melting point of the product is 184 to 185℃.
-Pratik Terse
4
Synthesis of Phenothiazine from
Diphenylamine.
Results:
• The practical yield was found to be _____grams and percentage yield
was _____percent and melting point was found to be ___degree Celsius.
Calculation:
Theoretical Yield:
Practical Yield:
% Practical Yield:
-Pratik Terse
5
• Derivatives of phenothiazine are
highly bioactive and have
widespread uses like promazine
and chlorpromazine as
antipsychotic drugs.
Uses:
-Pratik Terse
6

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Synthesis of Phenothiazine from Diphenylamine.pptx

  • 2. Synthesis of Phenothiazine from Diphenylamine. Aim: • To prepare and submit Phenothiazine from Diphenylamine. Requirements: • Apparatus: Round bottom flask, reflux condenser, water bath, oil bath. • Chemicals: Diphenylamine, Iodine, Ethanol, Charcoal, Sulphur. Theory: • Diphenylamine when treated with Sulphur undergo fusion reaction in the presence of iodine to give Phenothiazine a tricyclic compound used as an antihistamine engagement. -Pratik Terse 2
  • 3. Synthesis of Phenothiazine from Diphenylamine. Diphenylamine: • Molecular formula of Diphenylamine: C12H11N • Molecular wt. of Diphenylamine: 169 g/mol Phenothiazine: • Molecular formula of Phenothiazine: C12H9NS • Molecular wt. of Phenothiazine : 199 g/mol -Pratik Terse 3
  • 4. Synthesis of Phenothiazine from Diphenylamine. Procedure. • In a round bottom flask fitted with reflux condenser place 6.4 grams of Suphur, 16.8 gram Diphenylamine, and 300 mg Iodine. • Reflux the mixture on an oil bath at 190 to 200℃ for 30 to 40 minutes. • Cool and grind the residue mass in which 5 ml of ethanol and pinch of animal charcoal is added and heated it until solid mass dissolves. • Filter the solution while hot and cool in ice bath. • Filter the reaction mixture and obtain as yellow crystals of phenothiazine. • Melting point of the product is 184 to 185℃. -Pratik Terse 4
  • 5. Synthesis of Phenothiazine from Diphenylamine. Results: • The practical yield was found to be _____grams and percentage yield was _____percent and melting point was found to be ___degree Celsius. Calculation: Theoretical Yield: Practical Yield: % Practical Yield: -Pratik Terse 5
  • 6. • Derivatives of phenothiazine are highly bioactive and have widespread uses like promazine and chlorpromazine as antipsychotic drugs. Uses: -Pratik Terse 6