B. Sc.

III Year

Synthetic drug & dyes

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 Synthetic drug & dyes
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➢ Synthetic drugs :
Drug may be defined as a substance used in prevention, treatment,
diagnosis or cure of disease in human being or other animals.
➢ A drug may be single compound or combination of two or more compounds.
Ex. Paracetamol, Aspirin

➢ Qualities of good drug :

An ideal drug should satisfy the following conditions.
➢ i) It should be localized at the site where it is desired to act.
➢ ii) It should act on a system with efficiency and safety.
➢ iii) It should be nontoxic.
➢ iv) It should have minimum side effects.
➢ v) Drug should be easily available.
➢ vi) It should be less expensive.
➢ vii) It should not disturb physiological process.
❖ Classification of Drug :
Drugs are classified as follows :
❑ a) Functional drugs :
The drugs which are used to stimulate or depressed various
functions of body so as to provide some relief to body without
curing of disease.
Functional drugs are classified as follows.

➢ i) Analgesics :
The drugs which are used to reduce body pain without loss of
consciousness are called as analgesic drugs.
Ex.Aspirin, Ibuprofen, analgin

➢ ii) Antipyretics :
The drugs which are used to reduce the elevated body
temperature are called as antipyretic drugs.
Ex. Paracetamol

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➢ iii) Anaesthetics :
The drugs which are used to produce temporary
insensibility to human being are called as anaesthetic
drugs. There are two types of anaesthetic drugs.
➢a) General anaesthetic :
The drugs which are used to produce unconsciousness
and depression in central nervous system are call as
general anaesthetics.
Ex. Chloroform, divinyl ether, ethylene, cyclopropane,
avertin
➢b) Local anaesthetic :
The drugs which are used to produce an anaesthetic
effect to a limited area of the body when applied
externally or injected are called as local anaesthetics.
Ex. Lignocaine, xylocaine, cocaine, benzocaine etc
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➢ iv) Antidiabetics :
The drugs which are used to control the level of glucose in the blood
are called antidiabetics. This disease is caused due to deficiency of
effective insulin.
Ex.Tolbutamide, glycogen
➢ v) Anti inflammatory :
The drugs which are used to reduce inflammation in joint pains are
called anti inflammatory drugs.
Ex.Aspirin
➢ vi) Sedatives :
The drugs which are used to depress central nervous system without
producing sleep are called sedatives.
Ex.Veronal, bromatol, ethyl alcohol.
➢ vii) Hypnotics :
The drugs which are used to depress central nervous system with
producing sleep are called hypnotics.
Ex.Acetophenone, phenyl ethyl ketone, diethyl ketone, ethyl alcohol.
➢ viii) Tranquillizers :
The drugs which are used in the treatment of mental disorders are
called tranquillizers.
Ex. Chlorpromazine, reserpine, phenothiazine
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❑ b) Chemotherapeutic drugs :
The drugs which are used in the treatment and cure of specific
diseases are called chemotherapeutic drugs. They are classified as
follows :
➢ i) Antimalerials :
The drugs which are used to cure the malaria disease are called
antimalerials.
Ex. Chloroquine, pamaquine, quinine .
➢ ii) Antibacterials :
The drugs which are used in the treatment of infectious diseases
caused by bacteria are called as antibacterials.
Antibacterial drug may be bacteriostatic and bactericidal.
Bacteriostatic drugs which are used to inhibit the growth of bacteria
and bactericidal drugs which are used to kill the bacteria.
Ex. Sulphanilamide, sulpha drugs.
➢ iii) Antifungals :
The drugs which are used in the treatment of infectious diseases
caused by fungi are called as antifungals.
Ex. Salicylic acid, benzoic acid.

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iv) Antituberculars :
The drugs which are used in the treatment of tuberculosis known as
antitubercular drugs.
Ex. p-amino salicylic acid (PAS), isoniazide
v) Antibiotics :
It is a chemical substance produced from one micro-organism which
inhibit the growth of other infectious micro-organisms.
Ex. Penicillin, Cefixime, Streptomycin.
vi) Antiseptics :
The chemical substances which are used to prevent the sepsis of wounds
to kill the germs and harmful bacteria are called antiseptics.
Ex. Dettol (chloro xylenol), phenyl salicylate.
vii) Disinfectants :
The chemical substances which are used on non living objects to kill the
germs are called disinfectants.
Ex. Dettol (chloro xylenol), phenyl salicylate.
viii) Antivirals :
The drugs which are used in the treatment of infectious diseases caused
by viruses are called as antivirals.
Ex. Methisazone

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 Synthetic and uses of following drugs :
a) Paludrine : It is prepared from p-chloro aniline as follows
Cl Cl Cl
NH

NaNO2 / HCl H2N C NHCN

Cyanoguanidine
0-5 0C
Diazotisation - HCl, -N2 NH
NH2 N NCl HN C NHCN

p- chloro aniline diazotised p-chloroaniline

(CH3)2CHNH2
isopropyl amine
Cl

NH NH
HN C NH C NH CH(CH3)2

Paludrine
Uses : i) It is used as antimalerials.
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 b) Paracetamol : (4-hydroxy acetanilide)
p-amino phenol on acetylation with acetic anhydride gives paracetamol or
4-hydroxy acetanilide.

OH OH

(CH3CO)2O /
+ CH3COOH
CH3COONa

NH2 NHCOCH3
p-amino phenol Paracetamol

Uses : i) It is used as antipyretic.

ii) It is used as analgesic.

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c) Sulphanilamide (p-aminobenzene sulphonamide) :
Acetanilide is treated with chlorosulphonic acid it gives p-actamido
benzene sulphonyl chloride, which on react with NH3 gives p-actamido
benzene sulphonamide. Which on hydrolysis with NaOH gives
sulphanilamide.
NHCOCH3 NHCOCH3 NHCOCH3 NH2

HOSO2Cl NH3 NaOH

Acetanilide SO2Cl SO2NH2 SO2NH2

p-actamido benzene p-acetamido benzene Sulphanilamide
sulphonyl chloride sulphonamide

Uses : i) It is used as bacteriostatics .

ii) It is cheapest drug among all sulpha drug.

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d) Aspirin (Acetyl salicylic acids) :
Salicylic acid on Acetylation with acetic anhydride in the presence of
conc.H2SO4 gives Aspirin.

OH OCOCH3
Conc.H2SO4
+ (CH3CO)2O + CH3COOH

COOH COOH

Salicylic acid Aspirin

Uses : i) It is used as analgesic.

ii) It is used as antipyretic.
iii) It is used as anti inflammatory.

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e) Benzocaine (Ethyl ester of p-amino benzoic acid) :
p-nitro toluene on oxidation with KmnO4gives p-nitro benzoic acid.
Which on esterification with ethyl alcohol & HCl gives p-nitro ethyl
benzoate. This p-nitro ethyl benzoate on reduction with Sn/HCl gives
benzocaine.
CH3 COOH COOC2H5 COOC2H5

(O) C2H5OH/HCl Sn/HCl

KMnO4 Esterification Reduction

NO2 NO2 NO2 NH2

p-nitrotoluene p-nitro benzoic acid p-nitro ethylbenzoate Benzocaine

Uses : i) It is used as local anaesthetics.

ii) It is used to prevent nausea and vomiting.

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 f) Isoniazide :
4-methyl pyridine (picoline) on oxidation with KmnO4 yields isonicotinic
acid.Which on esterification with C2H5OH/H+ gives ethyl isonicotinate.
Further react with NH2NH2 gives isoniazide
CH3 COOH COOC2H5 CONHNH2

Oxidation C2H5OH NH2NH2

KMnO4 H2SO4
N N N N
4-methyl Pyridine Isonicotinic acid Ethyl Isonicotinate Isoniazide
(Picoline)

Uses :
i) It is used as antitubercular drug.

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 g) Sulphadiazine (2-sulphanilamidopyrimidine) :
2-amino pyrimidine react with p-acetamido benzene sulphonyl chloride
in the presence of pyridine followed by alkaline hydrolysis gives
sulphadiazine

N N
i) pyridine
+ ClO2S NHCOCH3
ii) alkaline
NH2 NH O2S NH2
N N
2-amino pyrimidine p-acetamido benzene
sulphonyl chloride Sulphadiazine

Uses : i) It is used as antibacterials.

ii) It is used in the treatment of meningitis disease.

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h) Tolbutamide :
It is prepared from p-toluene sulphonamide with urea, then esterification followed
by addition of n-butyl amine gives tolbutamide.
SO2NH2 SO2NHCONH2 SO2NHCONHCH2CH2CH2CH3
SO2NHCOOMe

NH2CONH2 / MeOH/H+ C4H9NH2

-NH3

CH3 CH3 CH3 CH3

p-toluene Tolbutamide
sulphonamide

Uses : It is used as antidiabetic drug (hypoglycemic agent)

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 B) Synthetic dyes :
➢ Dyes are those coloured compounds that can be firmly fixed
to the fabrics by chemical or physical bonding.
➢ All coloured compounds are not dyes.
➢ It is generally used for colouring of fibres , leathers, papers,
food & medicine.
➢ Classification of dyes :
Classification of dyes on the basis of methods of applications
as follows :
➢ a) Direct dyes :
These dyes can be applied by direct immersion of fabric into
hot solution of the dye. Then it is removed and dried.
A direct dye contains acidic or basic auxochrome which
combines with the opposite polar group present in the
chemical structure of the fibre. Wool and silk are dyed by this
direct method.
Ex. Martius yellow, Cango red

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 b) Acid dyes :
 The cloth or fabric are stirred in the acidic solution of dye.
Then it is removed and dried.
 Acid dyes are the sodium salt of acid. It contains sulphonic
acids or phenolic acids. The colour of the acid dyes are due to
the negative ions in their chemical structure.
 Ex. Picric acid, orange-II
 c) Basic dyes :
 The cloth or fabric are stirred in the basic solution of dye.
Then it is removed and dried. Basic dyes containing the basic
amino group (-NH2) and it is protonated in the acidic condition
of fibres by the formation of salt linkage with acidic group of
fibres.
 Ex. Methylene blue, Methyl violet.
 d) Vat Dyes :
 These dyes are insoluble in water but on reduction it is soluble
in water. Such dyes are used to dye the vegetables and animal
fibres directly.
 Ex. Indigo dye, Anthraquinone dye.
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 e) Mordent dyes :
 This class of dyes have no natural affinity for direct dye to the
fabric but their salts are used as dyes. Common used mordent
dyes are oxides of aluminium, iron or chromium. These salts
are called as mordent dyes. Mordent dye may be used to dye
wool, silk, cotton & nylon.
 Ex. Alizarin
 f) Developed Dyes / Azoic dyes / Ingrain dyes :
 These dyes are synthesized within the fabric and may be
applied to any type of fibre. The cloth is first soaked in alkaline
solution of phenol and dried. Then it is immersed in a cold
alkaline solution of a diazonium salt. Coupling reaction take
place in the fabric. Azoic dye may be used to dye cotton & other
cellulose fibres.
 Ex. Azo dye

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One mole of phthalic anhydride react with two moles of phenol in the
presence of conc. H2SO4 or anhydrous ZnCl2 at 1200C gives
Phenolphthalein. OH

O OH
C
H2SO4
O + 2 C OH
0
120 C
C O
O C
Phenol
Phthalic anhydride Phenolphthalein
O

Uses : i) It is used as acid base indicator.

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 Sulphanilic acid on diazotization with NaNO2/ HCl at 0-50C
gives diazotized sulphanilic acid. Which on coupling with
N,N-dimethyl aniline in NaOH gives methyl orange.
N(CH3)2

NH2 N2Cl N(CH3)2

NaNO2/HCl N
N Methyl Orange
0-50C NaOH

SO3H SO3H
Sulphanilic acid Diazotised
sulphanilic acid SO3Na

Uses : i) It is used as indicator in acid base titration.

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 Phthalic anhydride heated with catachol in the presence of conc. H2SO4
gives alizarin.
O OH O OH
C C
OH OH
O + Conc. H2SO4
C
C
O
Phthalic anhydride Catachol O
Alizarin

Uses : i) It is used to dye wool & cotton. ii) It is used in manufacture of printing ink.

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 It is prepared by coupling tetraazotised benzidine with two
molecules of naphthionic acid.
NH2 NH2

+ ClN2 N2Cl +

SO3H Tetraazotised benzidine SO3H

Naphthionic acid Naphthionic acid
Coupling

NH2 NH2

N N N N

SO3H Cango Red SO3H

Uses : i) It is used as dye.

ii) It is also used as indicator.
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 It is prepared by the reaction of one mole of benzaldehyde with two
moles of N,N-dimethyl aniline in the presence of conc. H2SO4
followed by oxidation with PbO2 gives malachite green.
H N(CH3)2
N(CH3)2
H
H2SO4
C O + CH
-H2O
N(CH3)2
H N(CH3)2
Leuco base

O PbO2

_ OH
+ HCl
C N(CH3)2Cl C N(CH3)2
-H2O

N(CH3)2 N(CH3)2
Malachite green Colourless

Uses : i) It is used as direct dye for wool and silk.

ii) It is also used as mordent dye for dyeing cotton and tannin.
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 It is obtained by coupling diazotized sulphanilic acid with
β-naphthol in NaOH. SO3H

N2Cl
N
OH N

+ NaOH OH

+ HCl
SO3H
B-naphthol
Diazotised sulfanilic Orange II
acid

Uses :
It is used to dye for wool, silk, nylon, paper & leather.
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 It is prepared as follows.
O O O H
N
Zinc dust Oxidation
CH3COOH [O]
N Cl N N
Isatin chloride H H O
Indoxyl (2 moles) Indigo

Uses : It is used to dye for wool and silk.

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 NH2
HO N NCl +

HOOC
Diazotised 5-amino
salicylic acid
1-naphthylamine

HO N N NH2

HOOC

NaNO2/HCl

HO N N N NCl

NaOOC

OH

1-naphthol
5-sulphonic acid

SO3H
OH

HO N N N N

NaOOC
SO3H

Uses : It is used toDiamond

dye wool,
black F
silk, cotton & nylon.
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According to Otto Witt theory the colour and chemical constitution of dyes are
based on Chromophore and Auxochrome. Therefore this theory is also called as
‘Chromophore-Auxochrome’ theory.
The colour of organic compounds is due to the presence of certain multiple
bounded unsaturated functional groups called Chromophores.
A few important chromophore groups are :
, -NO2 , N O , N N ,

Nitro Nitroso Azo

p-Quinoid
O O

C C C C
n
It has been noted that the presence of chromophore is not necessarily sufficient
for colour.
To make a substance coloured, the chromophore has to be conjugated with
aromatic rings. Thus, nitromethane is colourless while 2-nitronapthalene is
yellow.
CH3-NO2 Nitromethane ( Colourless )
NO2

2- Nitronapthlene ( Yellow ) 27
Certain functional groups (which are not chromophores) along with
chromophores, increases the intensity of colour. Such groups are called
auxochrome.
The auxochrome are two types i.e. acidic and basic as follows.
Acidic auxochromes : -OH, -SO3H, -COOH
Basic auxochromes : -NH2, -NHR, -NR2
Ex. 1) Azobenzene has red colour, while p-hydroxy azobenzene is bright red.
Chromophore Auxochrome

N N N N OH

Azobenzene p-hydroxy azobenzene

( Red ) ( Bright Red )

2) Nitrobenzene is a pale yellow coloured but when the auxochrome –OH is

attached to para position, the product becomes deep yellow.

NO2 HO NO2

Nitrobenzene p-nitro phenol

(Pale yellow) (Deep yellow)
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 Armstrong theory (Quinonoid theory)
Armstrong, in 1885 suggested that all colouring matters may be represented
by quinonoid structures. He said that the compound containing quinonoid
structure then it produces colour otherwise it is colourless. On the basis of this
theory we can say that benzene is colourless whereas benzoquinone is
coloured compound. O

Benzene O p- Benzoquinone
(Colourless) (yellow)

This theory explains very well the colouring properties of phenolphthalein.

Phenolphthalein is coloured when present in p-quinonoid structure but
colourless when p-quinonoid structure is absent.
OH O

C OH C O

O O
C C

O Phenolphthalein O Phenolphthalein
(colourless) (red coloured)
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Limitations :
i) This theory can not be explain colouring characteristics of all the compounds
Ex. Iminoquinone & di-iminoquinone both possess a quinonoid structure but
they are colourless. O NH

NH NH
Iminoquinone di-iminoquinone

ii) A number of compounds shows colour without quinonoid structure.

Ex.
CH2

O O
C6H5 N N C6H5
H3C C C CH3

diacetyl azobenzene
fulvene

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