This document describes the synthesis of benzanilide from aniline via a Schotten-Baumann reaction. Aniline reacts with benzoyl chloride in the presence of sodium hydroxide to form benzanilide and hydrochloric acid. The reaction involves benzoylation, where the benzoyl group is inserted in place of the active hydrogen on the amine group of aniline. Details of the reaction mechanism, chemicals used, equipment needed and procedure for synthesizing benzanilide are provided. The theoretical and percent yields are also calculated.

1. By:
Mrs. D. R. Mali
Asssitant Professor
Pharmaceutical Chemistry
GES’s Sir Dr. M. S. Gosavi College of
Pharmaceutical Education and Research,
Nashik.

2.  To synthesize benzanilide from aniline
 Laboratory Manual of Organic Chemistry by
Raj K. Bansal, Page No.111.
 Frederick George Mann and Bernard Charles
Saunders, ‘Practical Organic Chemistry’, IVth
edition Longman Group Limited, London,
1978, pp. 245

3. C
ClO
+
NH2
NaOH
+ NaCl +H2O
Benzoyl Chloride
Aniline Benzanilide
C
O
NH

4.  Benzoylation: Insertion of benzoyl moiety
instead of an active hydrogen atom present
in hydroxyl (OH) primary amino (NH2) or
secondary amino group (NH).
 Schotten Baumann reaction: Benzoylation of
compounds those are containing active
hydrogen such as Phenol, aniline, alcohol
etc. form benzoyl chloride in the presence of
aqueous NaOH
 Use:
It is used as fungicide and acaricide
(pesticide that kill ticks and mites).

5. Step 1: The formation of a
protonated compound
Step 2: The catalyst of the reaction
(i.e. the base) proceeds to absorb
the acidic proton
Step 3: In the final step, the
required amide product is formed
along with hydrochloric acid

7. C
Cl
O
H2N
C N
O
Cl H
H
C N
O
Cl H
H
C NH
O
H
Cl
C NH
O
Benzanilide
+ HCl

8. C
Cl
O
H2N
C N
O
Cl H
H
C N
O
Cl H
H
C NH
O
H
Cl
C NH
O
Benzanilide
+ HCl

9.  Chemicals:
 Aniline – 2 ml
 10% NaOH -30 ml
 Benzoyl chloride – 3 ml
 Cold water
 Hot alcohol
 Apparatus:
 Conical flask – 250 ml
 Buchner funnel
 Measuring cylinder
 Filter paper

10.  Place 2 ml (2.08 g) of aniline 30 ml of 10% NaOH
solution in 250 ml conical flask.
 Add 3 ml (3.4 g) of Benzoyl chloride slowly with
vigorous shaking.
 Cork the flask and shake for further 15-20 min or
till the odour of benzoyl chloride can no longer
be detected.
 Dilute the reaction mixture with cold water.
 Filter the crude benzanilide with suction on a
Buchner funnel.
 Wash with cold water and crystallize from hot
alcohol.
 Dry the product and calculate the percentage
yield.

11.  Molecular formula of aniline = C6H7N
 Molecular formula of benzanilide =
C13H11ON
 Molecular weight of aniline = 93 g/mole
 Molecular weight of benzanilide = 197
g/mole

12.  Theoretical yield:
93 g aniline forms 197 g benzanilide
 Therefore, 2.08 g (2 ml) aniline will form
………? (X) g benzanilide
 X = ( 197 × 2.08)/93 = 4.4 gs
 Theoretical yield = 4.4 gs
 Practical yield = ————- gs
 % Yield = (Practical Yield)/(Theoretical Yield)
× 100

13.  Name of compound: Benzanilide
 Structure:
 IUPAC Name: N-phenylbenzamide
 Molecular Formula: C13H11ON
 Molecular Weight: 197 g/mole
 Theoretical Yield: 4.4 g
 Practical Yield: ____ g
 Percentage Yield: _____ %
 Melting point: ___°C (162 to 164 °C)
C NH
O