Preparation of phenothiazine

Learn how to prepare phenothiazine from diphenyl amine with its principle and procedure. Explore this full laboratory guide.

It is a heterocyclic organic compound. It consists of two benzene rings fused to a central sulfur-containing ring. Structure of phenothiazine is:

phenothiazine structure

And its derivatives are used as antipsychotic medications, antiemetics and in the treatment of various medical conditions.

Preparation of phenothiazine from diphenyl amine

Firstly, for preparation these requirements are needed.

  • Round bottom flask.
  • Reflux condenser.
  • Water bath.
  • Oil bath.
  • Diphenyl amine,
  • Iodine.
  • Ethanol.
  • Charcoal.

Principle

When Diphenyl amine treated with Sulphur undergo fusion reaction in the presence of iodine to give phenothiazine, a tricyclic compound used as an antihistaminic agent.

synthesis of phenothiazine

Preparation procedure

  • Fit a reflux condenser with a round bottom flask.
  • Place 6.4 gm Sulphur, 16.8 gm of diphenyl amine and 300 mg iodine.
  • Reflux the mixture on an oil bath at 190-200°C for 30-40 minutes.
  • Cool and grind the residue mass.
  • Now add 5 ml of ethanol and pinch of animal charcoal.
  • Heat it until solid mass dissolves.
  • Filter the solution while hot.
  • Now cool the solution in ice bath.
  • Again, filter the reaction mixture and you will obtain yellow crystals of phenothiazine. Melting point of the product is 184-185°C.

Now, calculate the percentage yield and theoretical yield:

preparation of phenothiazine

After calculation submit the reports as:

The yield of obtained product was found to be ….. gm and percentage yield was ….% and melting point was found to be ……… °C.

Uses: Derivatives of phenothiazine are highly bioactive and have widespread uses like Promazine and Chlorpromazine as antipsychotic drugs.

You may also like to read Preparation of Phenacetin.

Leave a Comment