Preparation

of
Benzanilide
Content:-

- An introduction to Benzanilide.
- Solubility of Benzanilide.
- Uses of Benzanilide.
- Preparation methods.
- Mechanism.
- Procedure.
Benzanilide.
1- Benzanilide is a secondary fully aromatic amide,
with chemical formula (C13H11NO), molecular
weight (197) and structural formula:-

O
1- Benzanilide

NH
2- N- Phenyl-benzamide.
3- N-benzoylaniline.

2- Benzanilide is a solid organic compound with

yellow-green crystals, an odorless with the melting
point (M.P= 164-165C) and (B.P=247 C) .
Solubility and uses benzanilide
Homework????
Preparation methods
1-Reaction of aniline and benzoyl chloride.

O Cl
NH2
O

10% NaOH
+ NH + HCl
Or Pyridine

Aniline benzoyl chloride Benzanilide

2-Reaction of aniline with an ester:-

O OR
NH2
O

+ NH + ROH

Aniline An ester Benzanilide Alcohole

3- Reaction of aniline with Benzoic acid.

O OH
NH2
O

+ NH + H2O

Aniline Benzoic acid Benzanilide

Mechanism
O H
NH2 O
Cl C
N C

10%NaOH H Cl
+
Deprotonation

Aniline Benzoyl chloride H

O
1- Formation a new bond.
O
NH N C

Benzanilide H Cl
+

Cl 2- Breaking a bond.
+

H HCl + NaOH NaCl + H2O

Procedure:-
1- In a clean & dry conical flask dissolve (2ml) of aniline in
(20ml) of (10% NaOH).
2- Add (3ml) of benzoyl chloride to the solution.
3- Enclose the conical flask then shake the solution to about
(12)minutes.
4- Separate the produced benzanilide from the solution by
filtration process.
5- Wash the precipitate with distilled water several times, each
time (10ml) D.W.
6- Dry, weight out then calculate the percentage of yield of the
prepared benzanilide.