Amides

Presented by:
Hina Sharif
Lecturer Pharmaceutical Chemistry
 Amides
Amides are derivatives of carboxylic acids
in which a nitrogen group (—NH2) of a
primary or secondary amine replaces the
hydroxyl (—OH) group of carboxylic acids.

O CH3 O CH3
—C—OH —C—NH2
 Amides

Classification of amides
Amides may be primary, secondary, or tertiary
 Nomenclature of Amides
 In both the common and IUPAC names, amides are named by dropping the oic acid
(IUPAC) or ic acid (common) from the carboxylic acid name and adding the suffix
amide.
 Alkyl groups attached to the nitrogen of an amide are named with the prefix N
followed by the alkyl name.
Nomenclature of Amides

O CH3 —CH2

—CH2 —C—NH—CH3
ANALYZE Given Need
THE amide IUPAC name
PROBLEM
 Nomenclature of Amides
Give the IUPAC name for the following amide:
O
CH3—CH2—CH2—C—NH—CH3

STEP 1 Replace oic acid (IUPAC) or ic acid common) in the carboxyl name
with amide.

O CH3—CH2

—CH2—C—NH—CH3

butanamide
 Nomenclature of Amides
Give the IUPAC name for the following amide:
O
CH3—CH2—CH2—C—NH—CH3

STEP 2Name each substituent on the N atom using the prefix N and the alkyl
name.

O CH3 —CH2

—CH2 —C—NH—CH3

N-methylbutanamide
 Physical Properties of Amides
 Almost all amides are white, odorless (when
pure), crystalline solids.
 They have sharp melting points that are higher
than those of corresponding acids, owing to
intermolecular hydrogen bonding.
 As compared to primary amides, secondary and
tertiary amides have lower melting points, with
tertiary amides having lower melting points than
secondary amides (less opportunity for H-bonding).
 Simple amides upto six carbons are very soluble in
water but the water solubility declines as we
ascend the series.
 Identification tests of
Amides
 Boil the suspected amide with dilute sodium hydroxide solution
 ammonia evolved on boiling (no heat required to form ammonia, if it
was an ammonium salt)

RCONH2 + NaOH RCOONa + NH3

 aratio n
o f pre p
Metho d
1) Reaction of amines with acid chlorides

2) Reaction of acid anhydride with amines

3) From hydrolysis of nitriles
The hydrolysis of nitriles is a satisfactory method for preparation of unsubstituted amides and is
particularly convenient when hydrolysis is induced under mildly basic conditions by hydrogen peroxide:
 o ns
ea cti
ca l R
e m i
Ch
1) Hydrolysis of esters
Esters require more vigorous conditions for hydrolysis in both acid and base than esters.

2) Formation of esters from amides

3) Reduction

4) Dehydration
 Pharmaceutical Applications of
Amides
 Urea is one of the simplest amides, formed by reaction between CO2 and ammonia
in a series of metabolic reactions.

 Acetominophen is an aromatic amide Urea

 Barbiturates derive from barbituric acid (sedatives/tranquilizers) are cyclic

amides, made from urea and malonic acid:

2H2O

Urea
Pentanedioic acid
Malonic acid
Barbituric acid
 Pharmaceutical Applications of Amides
Penicillin is a beta lactam antibiotic
Bupivacaine is a local anesthetic
Saccharin and aspartame is used as artificial sweetener.