Benzocaine

COOEt

H2N

Benzocaine is a local anaesthetic compound, used as Appetite suppressants,

Astringents (compounds that tend to shrink body tissue), analgesics, burn and sun-

burn remedies, cough tablets, haemorrhoidal (these are vascular structures in the anal

canal which help with stool control, creates problem when swollen) creams, oral and

gingival products for teething and antibacterial agents.

 COOEt

SYNTHESIS H2N

Benzocaine is synthesized from toluene in a few steps:-

1. Nitration of toluene:

Me Me
HNO3
H2SO4
O2N

2. Reduction of NO2:

Me H2 Me

O2N Pd, C H2N

3. Oxidation of –Me gp. :

Me KMnO4 COOH

H2N H2N

4. Esterification :

COOH EtOH, H COOEt

H2N H2N
Benzocaine
 Fischer Esterification mechanism of formation of benzocaine

O OH CH3CH2OH OH
C OH OH
H SO3OH OH
O Et
H2N H2N H2N H

HSO4

OH
OSO3H
OH OH OH
OEt
OH2
OEt OEt H2N

H2N H2N
H SO3OH

OCH2CH3

H2N
 Characterisation Techniques:

1H-NMR:
2. GC-MS
Retention time : 18.94 min.
m/z - 165 (M+)
120 (100%) loss of –OCH2CH3
92 (ion lacking the ester group)
3. I.R.

-NH stretching 3424, 3346 → indicates presence of N-H bond

-CH stretching 3225 → indicates presence of C-H bond of
benzene ring
-C=O stretching 1687 → shows ester gp. of benzocaine
 Saccharin
(1,2 Benzisothiazol-3(2H)-one 1,1-dioxide)

NH
S O
O

It is a famous artificial sweetener. It is much sweeter than sucrose. It is used

to sweeten products such as drinks, candies, cookies, medicines and

toothpaste.
 SYNTHESIS

Steps in the synthesis of saccharin:

1. Chlorosulphonic acid gives a mixture of ortho- and para- products.

Me Me Me

ClSO2OH SO2Cl ClO2S

2. The sulfonyl chloride reacts with NH3 to give sulphonamides. Then –Me is
oxidised to –COOH using KMnO4 and finally dehydration gives saccharin.

Me NH3 Me KMnO4 COOH

SO2Cl SO2NH2 SO2NH2

-H2O

NH
S O
O
Saccharin
MECHANISM :

O O O O O O O
O
S S S S
HO Cl O Cl H2O Cl Cl

Me O Me O
Me O O
O O S
S
S Cl
H Cl
Cl

((NH4)2CO3

O HCl Me
COOH KMnO4

NH NH2 NH2
S (O) S
S O
O O O O
O
CHARACTERISATION :

1H-NMR
2. GC-MS :
m/z
183
(M+)

76
(100%)

92
(loss of NH and SO2)

119
(loss of SO2)
3. I.R.

3399 O-H stretching

3094 C-H stretching
1680 C=C stretching
1256 SO2 stretching
1600 C=O stretching
 THYROXINE
(Tetraiodothyronine)
T3 T4
Tyrosine I
I I
HO
COOH HO HO
O O
COOH COOH
NH2
I I
I I NH2
NH2

Thyroxine (3,5,3’,5’-tetraiodothyronine, T4) one of the two major hormone (T3, T4)

secreted by the thyroid gland. Its function is to release of unusual amino acids and

stimulate the consumption of O2. Thus helps in the metabolism of all cells and

tissues in the body.

Excessive secretion of T4 is known as hyperthyroidism or goitre.

Deficient secretion of T4 is called hypothyroidism.

SYNTHESIS
NO2 NO2
HO HNO3 HO Ac2O
COOH HO
COOH COOH
NH2 O2N NH2 O2N NHAc

EtOH, H+

OH
NO2 NO2
MeO TsO TsCl HO
CO2Et CO2Et

C5H5N C5H5N O2N NHAc

O2N NHAc

NO2 NH2
O H2,Pd O
CO2Et CO2Et

NHAc NHAc
MeO O2N MeO H2N

Diazotisation
HNO2

N2+
I
NaI, I2 O CO2Et
O CO2Et
+ NHAc
NHAc MeO N2
MeO I

HI,AcOH

I I
O COOH I O COOH
NH2 NH2
MeO I HO I
I
CHARACTERISATION :

1H-NMR
2. GC : Retention time – 5 min.
m/z 777 (M+)
3. IR
 SALBUTAMOL

OH
H
N
HO

HO

Salbutamol is a short acting β2-adrenergic receptor agonist used for relief from

asthma and chronic pulmonary disease.

It was the first selective β2-adrenergic receptor agonist to be marketed in 1968.

SYNTHESIS

It is synthesized from aspirin which itself is made by the acetylation of salicylic

acid.
O
HOOC Ac2O, H+ HOOC AlCl3 HOOC

HO O Fries rearrangement HO

O
O
O OH Br--Br Br
Br2 HOOC
HOOC HOOC
CHCl3
enolisation HO
HO HO

SN2 HN

Ph
O
Ph HOOC N
OH LiAlH4
H2,Pd/C HO N
HO
Hydrogenolysis HO

OH
H
HO N

HO
CHARACTERISATION :
1H-NMR
2. GC-MS :
m/z 239 (M+)
30 (100%)
CH3NH
86 (loss of
3. IR