Synthesis, antimicrobial activity and application of some novel quinazolinone based monoazo reactive dyes on various fibres

Article abstract of DOI:10.1016/j.dyepig.2010.10.013

The main target of this paper was to synthesize novel reactive dyes that not only give good dyeing property but also show pharmacological activity i.e. antimicrobial activity (antibacterial and antifungal). In this regard ten novel monoazo quinazolinone based reactive dyes (7a-j) were made by coupling of diazotised 3-{4-[4-amino-2-nitrobenzyl]-3-nitrophenyl}-7-chloro-2- phenylquinazolin-4(3H)-one (4) with various p-chloro anilino cyanurated coupling components (6a-j). The structures of all these synthesized dyes were confirmed by elemental analysis and spectral methods. The antimicrobial activity, colorimetric data, solvent effect and fastness properties of these dyes were also investigated.

Full text of DOI:10.1016/j.dyepig.2010.10.013

Dyes and Pigments 90 (2011) 1e10
Contents lists available at ScienceDirect
Dyes and Pigments
journal homepage: www.elsevier.com/locate/dyepig
Synthesis, antimicrobial activity and application of some novel quinazolinone
based monoazo reactive dyes on various fibres
*
Divyesh R. Patel, Keshav C. Patel
Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, Veer Narmad South Gujarat University, Surat 395 007, Gujarat, India
a r t i c l e i n f o
a b s t r a c t
Article history:
The main target of this paper was to synthesize novel reactive dyes that not only give good dyeing
property but also show pharmacological activity i.e. antimicrobial activity (antibacterial and antifungal).
In this regard ten novel monoazo quinazolinone based reactive dyes (7aej) were made by coupling of
diazotised 3-{4-[4-amino-2-nitrobenzyl]-3-nitrophenyl}-7-chloro-2-phenylquinazolin-4(3H)-one (4)
with various p-chloro anilino cyanurated coupling components (6aej). The structures of all these
synthesized dyes were confirmed by elemental analysis and spectral methods. The antimicrobial activity,
colorimetric data, solvent effect and fastness properties of these dyes were also investigated.
Ó 2010 Elsevier Ltd. All rights reserved.
Received 27 August 2010
Received in revised form
6 October 2010
Accepted 7 October 2010
Available online 18 November 2010
Keywords:
Antimicrobial activity
Colorimetric data
Solvent effect
Fastness properties
1. Introduction
All melting points are uncorrected and are expressed in ꢀC. TLC
analysis was carried out on silica gel G F254-precoated aluminum
The compound having fused heterocyclic system like 4(3H)-
quinazolinone and its derivatives are known to possess good
pharmacological activities and are also used as intermediates in the
dyestuff industry [1e5]. The dyes containing heterocyclic moiety
like quinazolinone have been found to give a wide range of color
shades (yellow to red) with very good depth and levelness on
fabrics and also showed excellent brightness and good fastness
properties like sublimation, washing and light and also show high
thermal stability [6,7].
In continuation of our interest in the direction of synthesis of
reactive dyes based on quinazolinone moiety [8,9], the present
paper deals with the facile and convenient synthesis of novel qui-
nazolinone reactive dyes and study of their dyeing properties,
fastness properties, antimicrobial activity, colorimetric data and
solvent effect are reported.
sheets [10]. IR spectra were recorded on a PerkineElmer Model 377
system using the potassium bromide wafer technique. Both 1H and
13C NMR spectra were determined on Bruker Avance II 400 MHz in
DMSO-d6 solvent using TMS as internal standard, UVevis absorp-
tion spectra were recorded on a Thermo Scientific Evolution 300
Spectrophotometer at the wavelength of maximum absorption
(
lmax) in a range of solvents, i.e. water, DMF, methanol, DCM and
chloroform at the various concentrations (1 ꢁ 10ꢂ6e10ꢂ8).
Elemental analysis (C, H and N) was carried out using C, H and N
analyzer, Carlo Erba, Italy. The dyeing was done by using Laboratory
Rota Dyer instrument.
Colorimetric data (L*, a*, b*, C*, H* and K/S) were recorded on
Reflectance Spectrophotometer Gretag Macbeth CE: 7000. Anti-
microbial activity (antibacterial and antifungal) was performed
using broth dilution method [11].
2.2. Synthesis of 4,40-methylene bis(m-nitro aniline) (1)
2. Experimental
m-Nitro aniline (13.8 g, 0.1 mol) was dissolved in water (125 ml)
and 36.5% hydrochloric acid (25 ml) at 50 ꢀC. The reaction mixture
was then reacted with 3% aqueous formaldehyde (35 ml) solution
at 60 ꢀC with stirring for 1 h and neutralized with 10% sodium
hydroxide solution. The reddish precipitates obtained were filtered,
washed with hot water, dried and recrystallized from acetic acid.
Yield 78%, m.p. 65e68 ꢀC. TLC: Rf ¼ 0.75 (PhMe:EtOAc, 3:1 v/v). IR
(KBr) cmꢂ1: 3430, 3385 (NeH), 3097 (CeH), 1625 (NeH bend.),
2.1. Materials and methods
The coupling components used for the synthesis of dyes were
received from Atul Ltd., Gujarat, India. The solvents used were of
spectroscopic grade.
* Corresponding author. Tel.: þ91 261 2258384; fax: þ91 261 2256012.
E-mail address: divyeshpatel_905@yahoo.com (K.C. Patel).
0143-7208/$ e see front matter Ó 2010 Elsevier Ltd. All rights reserved.
doi:10.1016/j.dyepig.2010.10.013

2
D.R. Patel, K.C. Patel / Dyes and Pigments 90 (2011) 1e10
1523, 1349 (N]O). 1H NMR (DMSO-d6)
6.28 (4H, s, NH2), 6.95e7.42 (6H, m, AreH). Anal. Calcd. for
C13H12O4N4 (288.26): C, 54.17%; H, 4.20%; N, 19.44%, found, C,
54.11%; H, 4.14%; N, 19.38%. (Scheme 1).
d
ppm: 2.38 (2H, s, CH2),
of water (25 ml), conc. HCl (1.88 ml, 0.015 mol) and ice (10 g). The
reaction mixture was cooled to 0e5 ꢀC using an ice bath. NaNO2
(0.35 g, 0.005 mol) dissolved in water (10 ml) was then added drop-
wise. The solution was stirred for 30 min and excess HNO2 was
decomposed by adding sulphamic acid. Activated carbon was added
with stirring and the mixture was filtered at 0e5 ꢀC to give the clear
yellow solution (4). (Scheme 2).
2.3. Synthesis of 7-chloro-2-phenyl-4H-benzo[1,3]
oxazine-4-one (2)
To a stirred solution of 4-chloro anthranilic acid (1.72 g,
0.01 mol) in pyridine (60 ml), Benzoyl chloride (1.16 ml, 0.01 mol)
was added dropwise, maintaining the temperature near 0e5 ꢀC for
1 h. The reaction mixture was stirred for another 2 h at room
temperature until a solid product was formed. The reaction mixture
was neutralized with saturated sodium bicarbonate solution. A
white solid which separated was filtered, washed with water and
recrystallized from ethanol. Yield 70%, m.p. 192e195 ꢀC. TLC:
Rf ¼ 0.68 (PhMe:EtOAc, 3:1 v/v). IR (KBr) cmꢂ1: 3075 (CeH), 1613
(C]N), 1756 (C]O), 1062 (CeOeC), 1177 (CeO), 779 (CeCl). 1H
2.6. Preparation of coupling components (5) and (6a)
H-acid (3.19 g, 0.01 mol) was dissolved in water (15 ml) at pH 7.5,
using 20% (w/v) Na2CO3. A solution of cyanuric chloride (1.85 g,
0.01 mol) in acetone (20 ml) was cooled to 0e5 ꢀC and added
dropwise to the stirred H-acid solution at 0e5 ꢀC (Scheme 1). After
10 min, the solution was adjusted to pH 4 by adding 20% (w/v)
Na2CO3, and the reaction was continued for 1 h at 0e5 ꢀC. The
progress of the reaction was followed by TLC using n-PrOH:n-
BuOH:EtOAc:H2O, 2:4:1:3, in which the product 5 had Rf ¼ 0.72.
(Scheme 3).
p-Chloro aniline (1.28 g, 0.01 mol) was added to a well-stirred
solution of 5 (0.01 mol) and after adjusting to pH 6.5 using 20%
(w/v) Na2CO3, the solution was stirred for 1 h at 40 ꢀC. The progress
of the reaction was followed by TLC (n-PrOH:n-BuOH:EtOAc:H2O,
2:4:1:3), where the 6a had Rf ¼ 0.36. (Scheme 3).
NMR (DMSO-d6)
d ppm: 7.58e8.03 (8H, m, AreH). Anal. Calcd. for
C14H8O2NCl (257.67): C, 65.26%; H, 3.13%; N, 5.44%, found, C,
65.22%; H, 3.08%; N, 5.38%. (Scheme 2).
2.4. Synthesis of 3-{4-[4-amino-2-nitrobenzyl]-3-nitrophenyl}-7-
chloro-2-phenylquinazolin-4(3H)-one (3)
4,40-Methylene bis(m-nitro aniline) (1.44 g, 0.005 mol) and 7-
chloro-2-phenyl-4H-benzo[1,3]oxazine-4-one (1.29 g, 0.005 mol)
were dissolved in pyridine (40 ml) and heated under reflux for 6 h
under anhydrous reaction conditions and then allowed to cool at
room temperature. The reaction mixture was then treated with ice
cooled dilute hydrochloric acid and stirred. A solid separated out
which was filtered off and washed with water to remove any
adhered pyridine. The crude quinazolinone thus obtained was
dried under vacuum and recrystallized from ethanol. Yield 72%,
m.p. 157e160 ꢀC. TLC: Rf ¼ 0.64 (PhMe:EtOAc, 3:1 v/v). IR (KBr)
cmꢂ1: 3425, 3380 (NeH) 3045 (CeH), 1613 (C]N), 1674 (C]O),
1494 (CeN), 1525, 1350 (N]O), 778 (CeCl). 1H NMR (DMSO-d6)
2.7. Synthesis of reactive dyes (7aej)
Freshly prepared diazonium salt solution (0.005 mol) (4) was
added dropwise to well-stirred solution of 6a (0.005 mol). The
solutions were maintained at pH 9 by adding 20% (w/v) Na2CO3 and
the coupling step was continued for 4 h at 0e5 ꢀC. Then, 10% (w/v)
urea was added [12] and the dyes were isolated by salting out of
solution using NaCl (12 g). The pH was adjusted to 7 using HCl (6%
w/v) and stirring was continued for 2 h. The dye was collected by
filtration and washed with 5% (w/v) NaCl. Salt was removed by
stirring the crude dyes with dimethylformamide (DMF), followed
by the dye precipitation by adding EtOAc to the filtrate. The dye 7a
was collected, washed with EtOAc and air dried. The eluent system
for TLC was 2-BuOH:EtOH:NH4OH:pyridine, 4:1:3:2. Dye 7a had
Rf ¼ 0.38, with minor impurities at Rf ¼ 0.20. (Scheme 4).
Same coupling procedure and condition was followed for other
reactive dyes 7bej were synthesized using p-chloro anilino cyan-
urated coupling components such as J-acid (6b), N-methyl-J-acid
(6c), N-phenyl-J-acid (6d), Bronner acid (6e), Gamma acid (6f),
Tobias acid (6g), Sulpho Tobias acid (6h), Peri acid (6i) and Koch
acid (6j). All the p-chloro anilino cyanurated coupling components
are summarized in Chart 1.
d
ppm: 2.28 (2H, s, CH2), 6.22 (2H, s, NH2), 7.52e8.06 (14H, m,
AreH). Anal. Calcd. for C27H18O5N5Cl (527.92): C, 61.43%; H, 3.44%;
N, 13.27%, found, C, 61.38%; H, 3.40%; N, 13.22%. (Scheme 2).
2.5. Preparation of diazonium salt solution (4)
3-{4-[4-amino-2-nitrobenzyl]-3-nitrophenyl}-7-chloro-2-phenyl-
quinazolin-4(3H)-one (2.64 g, 0.005 mol) (3) was stirred in a mixture
NO2
O2N
H
H
Characterizations of all the dyes 7a-j are given below:
C
O
H2N
NH2
+
+
(1) Dye 7a (p-chloro anilino cyanurated H-acid):
Dye 7a was obtained in 80% yield (Dark purple); Mp > 300 ꢀC;
Rf ¼ 0.38; IR (KBr)
1664 (C]O), 1595 (C]N), 1613 (N]N), 1530, 1346 (N]O), 1382,
1155 (S]O), 779 (CeCl); 1H NMR (400 MHz, DMSO-d6)
ppm: 2.60
(2H, s, CH2), 4.42 (1H, s, OH), 8.73 (2H, s, NH), 6.64e7.58 (21H, m,
AreH); 13C NMR (400 MHz, DMSO-d6)
ppm: 39.12, 39.44, 39.71
(CH2), 162.12 (C]O), 108.22, 112.75, 113.52, 116.28, 118.32, 119.20,
121.15, 124.12, 125.90, 128.30, 131.75, 132.20, 134.90, 136.65, 139.55,
141.30, 144.10, 146.52, 148.12, 152.22, 155.35, 164.90, 169.22 (Ar);
C46H26O12N11S2Cl3Na2 (1141.23): calc. C, 48.41%; H, 2.30%; N,
13.50%, found C, 48.33%, H, 2.22%, N, 13.44%.
n
cmL1: 3456 (OeH), 3326 (NeH), 3094 (CeH),
(ii) 10% NaOH
(i) HCl
d
d
O2N
NO2
NH2
H2N
CH2
(1)
Scheme 1. Preparation of dye intermediate (1).
(2) Dye 7b (p-chloro anilino cyanurated J-acid):

D.R. Patel, K.C. Patel / Dyes and Pigments 90 (2011) 1e10
3
O
N
O
C
COCl
COOH
OH
O
O
-H2O
Pyridine
0-5 °C
+
Cl
Cl
NH2
Cl
N
H
C
(2)
Now,
O
O2N
NO2
O
Pyridine
Reflux
NH2
H N
CH2
+
2
N
Cl
(1)
NO2
O2N
O
N
(2)
N
CH2
NH2
Cl
(3)
NaNO2 + HCl
0-5 oC
NO2
O2N
O
N
CH2
N2Cl
N
Cl
(4)
Scheme 2. Preparation of dye intermediates (2), (3) and (4).
Cl
N
Cl
N
N
OH
NH2
Cl
N
Cl
OH
NH
pH 4, 0-5 °C
Acetone
N
N
+
HO3S
SO3H
Cl
HO3S
SO3H
(5)
H
Cl
N
N
N
N
Cl
OH
NH
p
-Chloro aniline
pH 6.5, 40 °C
HO3S
SO3H
(6a)
Scheme 3. Preparation of p-chlro anilino cyanurated H-acid (6a).

4
D.R. Patel, K.C. Patel / Dyes and Pigments 90 (2011) 1e10
H
N
Cl
N
NO2
O2N
O
N
N
N
Cl
N
CH2
N2Cl
OH
NH
Cl
+
(4)
HO3S
SO3H
(6a)
H
N
pH 9
Cl
N
0-5 °C
N
N
Cl
NO2
O2N
O
N
OH
NH
N
CH2
N
N
Cl
NaO3S
SO3Na
(7a)
R
Where R=Various p-chloro anilino cyanurated coupling components (6a-j)
Scheme 4. Synthesis of dye 7a.
H
N
Cl
N
Cl
Cl
N
N
Cl
OH
NH
N
OH
NH
OH
NH
N
N
N
N
HO3S
N
Cl
HO3S
N
H
N
Cl
HO3S
SO3H
(6c)
CH3
(6a)
(6b)
Cl
Cl
Cl
H
N
NH
Cl
N
OH
NH
N
N
N
N
OH
N
N
N
N
Cl
HN
H
HO3S
N
N
Cl
HO3S
SO3H
(6f)
(6e)
(6d)
Cl
Cl
H
N
H
Cl
N
Cl
N
N
H
N
H
Cl
N
N
N
Cl
N
N
N
N
Cl
Cl
N
N
N
N
SO3H NH
SO3H
SO3H NH
SO3H
HN
HN
HO3S
SO3H
(6g)
(6i)
(6j)
(6h)
SO3H
Chart 1. Various p-chloro anilino cyanurated coupling components (6aej). (Arrow indicates the coupling position).

D.R. Patel, K.C. Patel / Dyes and Pigments 90 (2011) 1e10
5
ꢀ
Dye 7b was obtained in 78% yield (Reddish yellow); Mp > 300 C;
C46H27O9N11SCl3Na (1039.19): calc. C, 53.17%, H, 2.62%, N, 14.83%,
Rf ¼ 0.42; IR (KBr)
1683 (C]O), 1598 (C]N), 1622 (N]N), 1574, 1353 (N]O), 1382,
1158 (S]O), 779 (CeCl); 1H NMR (400 MHz, DMSO-d6)
ppm: 2.58
(2H, s, CH2), 4.63 (1H, s, OH), 8.23 (2H, s, NH), 7.46e7.69 (22H, m,
AreH); 13C NMR (400 MHz, DMSO-d6)
ppm: 39.10, 39.22, 39.52
(CH2), 162.25 (C]O), 109.12, 112.22, 113.60, 115.12, 120.22, 121.55,
122.95, 125.40, 128.15, 131.50, 133.10, 134.22, 135.50, 136.12, 139.44,
142.10, 144.45, 146.15, 150.25, 152.68, 156.50, 165.80, 170.06 (Ar);
C46H27O9N11SCl3Na (1039.19): calc. C, 53.17%, H, 2.62%, N, 14.83%,
found C, 53.11%, H, 2.55%, N, 14.78%.
n
cmL1: 3571 (OeH), 3318 (NeH), 3121 (CeH),
found, C, 53.10%, H, 2.57%, N, 14.75%.
d
(7) Dye 7g (p-chloro anilino cyanurated Tobias acid):
Dye 7g was obtained in 80% yield (Light yellow); Mp > 300 ꢀC;
d
Rf ¼ 0.38; IR (KBr)
1598 (C]N), 1620 (N]N), 1520, 1355 (N]O), 765 (CeCl); 1H NMR
(400 MHz, DMSO-d6) ppm: 2.50 (2H, s, CH2), 8.35 (2H, s, NH),
6.98e7.70 (24H, m, AreH); 13C NMR (400 MHz, DMSO-d6)
ppm:
n
cmL1: 3312 (NeH), 3015 (CeH), 1668 (C]O),
d
d
39.06, 39.26, 39.48 (CH2), 162.08 (C]O), 108.15, 110.24, 111.60,
114.20, 115.55, 119.12, 120.20, 123.24, 125.76, 129.52, 132.60, 133.40,
134.10, 135.34, 137.24, 138.58, 140.12, 144.65, 147.14, 150.10, 155.35,
166.08, 169.25 (Ar); C46H28O5N11Cl3 (921.14): calc. C, 59.98%, H,
3.06%, N, 16.73%, found, 59.92%, H, 3.01, N, 16.68%.
(3) Dye 7c (p-chloro anilino cyanurated N-methyl-J-acid):
ꢀ
Dye 7c was obtained in 77% yield (Reddish orange); Mp > 300 C;
Rf ¼ 0.36; IR (KBr)
1670 (C]O), 1596 (C]N), 1618 (N]N), 1540, 1322 (N]O), 1375,
1160 (S]O), 775 (CeCl); 1H NMR (400 MHz, DMSO-d6)
ppm: 2.42
(2H, s, CH2), 2.65 (3H, s, NeCH3), 4.45 (1H, s, OH), 8.38 (1H, s, NH),
7.12e7.60 (22H, m, AreH); 13C NMR (400 MHz, DMSO-d6)
ppm:
n
cmL1: 3485 (OeH), 3285 (NeH), 3035 (CeH),
(8) Dye 7h (p-chloro anilino cyanurated Sulpho tobias acid):
Dye 7h was obtained in 75% yield (Reddish yellow); Mp > 300 ꢀC;
d
d
Rf ¼ 0.40; IR (KBr)
1602 (C]N),1610 (N]N),1544,1360 (N]O), 1372, 1145 (S]O), 770
(CeCl); 1H NMR (400 MHz, DMSO-d6)
ppm: 2.45 (2H, s, CH2), 8.42
(2H, s, NH), 7.06e7.42 (23H, m, AreH); 13C NMR (400 MHz, DMSO-
d6) ppm: 39.20, 39.35, 39.58 (CH2), 162.20 (C]O), 109.20, 109.35,
n
cmL1: 3350 (NeH), 3012 (CeH), 1672 (C]O),
21.25, 21.38, 21.60, 21.72 (NeCH3), 39.25, 39.48, 39.60 (CH2), 162.68
(C]O), 109.12, 112.22, 114.10, 115.20, 117.22, 120.10, 121.40, 123.22,
125.75, 126.22, 128.35, 132.20, 133.38, 134.70, 135.12, 136.16, 138.58,
143.30, 144.25, 147.50, 150.25, 154.20, 155.16, 166.40, 169.80 (Ar);
C47H29O9N11SCl3Na (1053.22): calc. C, 53.60%, H, 2.78%, N, 14.63%,
found C, 53.54%, H, 2.72%, N, 14.58%.
d
d
111.60, 113.35, 115.22, 118.45, 121.55, 123.75, 125.55, 129.12, 131.78,
133.56, 135.80, 136.76, 138.55, 140.12, 143.54, 144.65, 146.07, 150.13,
154.15, 165.22, 169.42 (Ar); C46H27O8N11SCl3Na (1023.19): calc. C,
54.00%, H, 2.66%, N, 15.06%, found, C, 53.92%, H, 2.58%, N, 15.00%.
(4) Dye 7d (p-chloro anilino cyanurated N-phenyl-J-acid):
Dye 7d was obtained in 82% yield (Dark red); Mp > 300 ꢀC;
(9) Dye 7i (p-chloro anilino cyanurated Peri acid):
Rf ¼ 0.40; IR (KBr)p
n
cmL1: 3428 (OeH), 3258 (NeH), 3008
(CeH), 1672 (C]O), 1605 (C]N), 1610 (N]N), 1553, 1330 (N]O),
Dye 7i was obtained in 77% yield (Light yellow); Mp > 300 ꢀC;
1380, 1145 (S]O), 780 (CeCl); 1H NMR (400 MHz, DMSO-d6)
Rf ¼ 0.36; IR (KBr)
1608 (C]N), 1612 (N]N),1540, 1338 (N]O), 1370, 1138 (S]O), 765
(CeCl); 1H NMR (400 MHz, DMSO-d6)
ppm: 2.62 (2H, s, CH2),
8.55 (2H, s, NH), 7.10e7.62 (23H, m, AreH); 13C NMR (400 MHz,
DMSO-d6) ppm: 39.15, 39.32, 39.56 (CH2), 161.90 (C]O), 108.90,
n
cmL1: 3345 (NeH), 3020 (CeH), 1670 (C]O),
d
ppm: 2.38 (2H, s, CH2), 4.50 (1H, s, OH), 8.30 (1H, s, NH), 7.10e7.68
(27H, m, AreH); 13C NMR (400 MHz, DMSO-d6)
d
ppm: 39.10,
d
39.32, 39.55 (CH2), 161.80 (C]O), 108.44, 112.20, 114.15, 115.22,
118.09, 119.28, 121.30, 122.50, 123.34, 125.49, 126.60, 128.70, 130.21,
132.64, 134.30, 135.20, 139.67, 143.55, 144.20, 146.62, 148.14, 154.10,
156.22, 166.56, 169.03 (Ar); C52H31O9N11SCl3Na (1115.28): calc C,
56.00%, H, 2.80%, N, 13.81%, found, C, 55.96%, H, 2.76%, 13.75%.
d
110.12, 111.07, 113.15, 115.20, 119.22, 122.66, 123.43, 125.44, 128.78,
129.70, 130.25, 132.60, 133.50, 134.21, 136.83, 139.14, 140.66, 144.10,
145.03, 150.32, 154.45, 166.39, 169.11 (Ar); C46H27O8N11SCl3Na
(1023.19): calc. C, 54.00%, H, 2.66%, N, 15.06%, found, C, 53.94%, H,
2.59%, N, 15.02%.
(5) Dye 7e (p-chloro anilino cyanurated Bronner acid):
ꢀ
Dye 7e was obtained in 75% yield (Reddish yellow); Mp > 300 C;
Rf ¼ 0.42; IR (KBr)
1595 (C]N),1614 (N]N),1523,1340 (N]O),1384,1160 (S]O), 758
(CeCl); 1H NMR (400 MHz, DMSO-d6)
ppm: 2.59 (2H, s, CH2), 8.28
(2H, s, NH), 7.46e7.60 (23H, m, AreH); 13C NMR (400 MHz, DMSO-
d6) ppm: 39.22, 39.42, 39.60 (CH2), 161.98 (C]O), 109.15, 111.25,
113.82, 114.35, 118.56, 120.18, 125.45, 126.12, 127.66, 128.34, 129.78,
131.88, 132.22, 133.40, 134.56, 139.12, 140.95, 142.08, 146.44, 157.62,
158.10, 165.23, 169.12 (Ar); C46H27O8N11SCl3Na (1023.19): calc C,
54.00%, H, 2.66%, N, 15.06%, found, C, 53.95%, H, 2.60%, N, 15.01%.
n
cmL1: 3283 (NeH), 3031 (CeH), 1683 (C]O),
(10) Dye 7j (p-chloro anilino cyanurated Peri acid):
d
Dye 7j was obtained in 80% yield (Greenish yellow); Mp > 300 ꢀC;
Rf ¼ 0.38; IR (KBr)
1603 (C]N),1615 (N]N),1565, 1362 (N]O),1365,1175 (S]O), 770
(CeCl); 1H NMR (400 MHz, DMSO-d6)
ppm: 2.45 (2H, s, CH2),
8.45 (2H, s, NH), 7.22e7.85 (21H, m, AreH); 13C NMR (400 MHz,
DMSO-d6) ppm: 39.14, 39.35, 39.62 (CH2), 161.85 (C]O), 109.55,
n
cmL1: 3325 (NeH), 3010 (CeH), 1675 (C]O),
d
d
d
110.32, 111.34, 113.68, 114.12, 115.44, 116.80, 118.04, 120.60, 122.78,
123.65, 124.55, 125.80, 126.14, 129.77, 130.54, 134.12, 136.40, 140.43,
144.45, 151.20, 154.29, 165.22, 168.96 (Ar); C46H25O14N11S3Cl3Na3
(1227.28): calc. C, 45.02%, H, 2.05%, N, 12.55%, found, C, 44.95%, H,
2.00%, N, 12.48%.
(6) Dye 7f (p-chloro anilino cyanurated Gamma acid):
Dye 7f was obtained in 77% yield (Dark yellow); Mp > 300 ꢀC;
Rf ¼ 0.38; IR (KBr)
1672 (C]O), 1598 (C]N), 1612 (N]N), 1523, 1349 (N]O), 1385,
1169 (S]O), 775 (CeCl); 1H NMR (400 MHz, DMSO-d6)
ppm: 2.49
(2H, s, CH2), 4.52 (1H, s, OH), 8.41 (2H, s, NH), 7.21e7.78 (22H, m,
AreH); 13C NMR (400 MHz, DMSO-d6)
ppm: 39.09, 39.25, 39.50
n
cmL1: 3456 (OeH), 3292 (NeH), 3023 (CeH),
Abbreviation: s-singlet, m-multiplet.
d
3. Results and discussion
d
3.1. Spectral characteristics
(CH2), 162.22 (C]O), 109.12, 111.25, 112.56, 114.25, 118.70, 120.22,
123.68, 126.40, 128.75, 130.85, 132.55, 134.50, 135.20, 137.22, 139.10,
142.55, 144.05, 146.18, 150.44, 152.35, 155.60, 165.55, 169.32 (Ar);
The structures of all the dyes 7aej were confirmed by various
spectroscopic techniques, including IR, 1H NMR and 13C NMR.

6
D.R. Patel, K.C. Patel / Dyes and Pigments 90 (2011) 1e10
The IR spectra [13] of dyes 7aed and 7f showed characteristic
dyes 7a, 7c, 7d and 7f. These results suggest that the excited state in
these dyes were more polar than the ground state.
broad absorption band at 3428e3571 cmꢂ1 region corresponding
to the OeH stretching vibration of hydroxyl group. The band at
3258e3350 cmꢂ1 region corresponding to the NeH stretching
vibration of secondary amino group and another band at
1610e1622 cmꢂ1 region is due to the N]N stretching vibration of
azo group. Intermediate 2 showed carbonyl (C]O) stretching
vibration at 1756 cmꢂ1 while intermediate 3 and all the dyes 7aej
showed carbonyl stretching at 1664e1683 cmꢂ1, which confirmed
The hypsochromic shift (negative solvatochromism) occurring
in water related to DMF, ethanol, DCM and chloroform. This effect is
observed in dyes 7b, 7e, 7g, 7h, 7i and 7j. The negative sol-
vatochromism observed is due to the solute solvent interaction
through intermolecular hydrogen bond formation between water
and lone pair of electron of secondary amino nitrogen atom.
the formation of amide linkage via conversion of
d
d-lactone to
3.3. Acid and base effect on UVevis spectra
-lactum ring. The band at 1595e1608 cmꢂ1 showed the confir-
mation of C]N group of quinazolinone ring. Other characteristic
band of all the dyes 7aej appearing at 1520e1574, 1322e1362 cmꢂ1
are due to the asymmetric and symmetric N]O stretching of nitro
group, 1365e1385, 1138e1175 cmꢂ1 are due to the asymmetric and
symmetric S]O stretching of sulfonic acid group and
765e780 cmꢂ1 is due to the CeCl stretching of chloro group.
The 1H NMR spectra [14] of all the dyes 7aej were recorded in
The effect of acid and base on the absorption of dye solution was
investigated and the results are shown in Table 1.
The absorption spectra of the dyes in methanol were quite
sensitive to the addition of 0.1 M KOH. The lmax of all the dyes
(7aej) showed bathochromic shift by addition of 0.1 M KOH, this
suggests that these dyes were present in different tautomeric form
as in methanol. And when 0.1 M HCl was added to the dye solution
in methanol, all the dyes (7aej) showed large bathochromic shift
except dyes 7g and 7j. This showed that all the dyes except 7g and
7j exist in the cationic form in acidic methanolic solution.
When piperidine was added to the dye solution in chloroform
lmax of all the dyes (7aej) did not change significantly except dyes
7d and 7f. Dyes 7d and 7f shows large bathochromic shift when
piperidine was added to the solution of chloroform. (Absorption
spectra of dyes 7f in acidic and basic solution are shown in Figs. 3
and 4).
DMSO. All the dyes 7aej showed singlet at
which can be attributed to the methylene proton. The dyes showed
singlet at
¼ 4.42e4.63 ppm which can be attributed to the
phenolic proton except for dyes 7e and 7gej. All the dyes 7aej
showed singlet in the downfield at
d
¼ 2.38e2.62 ppm,
d
d
¼ 8.23e8.73 ppm which can
be attributed to amino proton, this downfield shift is probably due
to the intermolecular hydrogen bonding between amino group and
solvent (DMSO). The aromatic protons were observed from 6.64 to
7.85 ppm in the 1H NMR spectra.
The 13C NMR spectrum [14] of all the dyes 7aej showed triplet at
d
¼ 39.06e39.71 ppm, which can be attributed to methylene
carbons. Dye 7c showed quartet at
¼ 21.25e21.72 ppm which can
be attributed to methyl carbon of N-methyl group of coupler
moiety. Carbonyl carbon showed singlet at
¼ 161.85e162.68 ppm.
All the dyes 7aej showed characteristic band of aromatic carbon at
¼ 108.15e170.06 ppm.
3.4. Substituent effect
d
Absorption maxima of all the dyes (7aej) were recorded in
water and are shown in Table 1. The introduction of electron
donating or electron attracting groups at the suitable position in
the coupler ring affected the absorption characteristic of dyes. As
can be seen from the data in Table 1, the bathochromic shift can be
obtained by introducing methyl group in dye 7c, this gave consid-
erable shift of 5 nm relative to dye 7b. An additional bathochromic
shift of 15 nm can be obtained by introducing phenyl ring in dye 7d
relative to dye 7b. The introduction of auxochromic group like
sulfonic acid group which cause bathochromic shift by increase
polarisability in the dye molecule. Here bathochromic shift of
30 nm, 45 nm, 20 nm and 12 nm was observed by introducing
sulfonic acid group in dye 7e, 7f, 7h and 7i relative to dye 7g. The
lower absorption maxima value of dye 7j (435 nm) is due to the
moderating effect of three sulfonic acid group.
d
d
3.2. Solvent effect on UVevis spectra
The visible absorption spectra of all the dyes (7aej) in pure
solvents of different dielectric constant via water (78.39), DMF
(36.71), ethanol (24.55), dichloro methane (8.93) and chloroform
(4.81) were recorded and shown in Table 1, which showed that the
bands were observed in the region 430e530 nm in water,
422e522 nm in DMF, 415e515 nm in ethanol, 435e502 nm in
dichloro methane and 450e495 nm in chloroform. (Absorption
spectra of dyes 7a and 7f in different solvent are summarized in
Figs. 1and 2 respectively).
The bathochromic shift (positive solvatochromism) was
observed in water relative to DMF, ethanol, DCM and chloroform, is
a result of the increase in the solvent polarity because of the
increase in the dielectric constant of water relative to DMF, ethanol,
DCM and chloroform. This positive solvatochromism is observed in
3.5. Dyeing of fibres
All the dyes 7aej were applied on silk, wool and cotton fibres in
2% (owf) shade according to following procedure. The variation in
the hues of the dyed fibres results from changing the coupling
Table 1
Influence of solvent and effect of acid & base on lmax (nm) of dyes 7aej.
Dye no.
Water
DMF
Methanol
DCM
Chloroform
Methanol þ KOH
Methanol þ HCl
Chloroform þ Piperidine
7a
7b
7c
7d
7e
7f
7g
7h
7i
530
480
485
495
460
475
430
450
442
435
525
472
480
488
455
465
426
444
436
422
515
465
472
485
450
460
424
438
428
415
505
460
465
470
468
455
440
452
435
440
490
475
456
462
478
445
462
465
450
468
530
475
482
498
462
470
435
445
432
428
542
495
492
505
472
490
426
460
450
418
492
478
456
495
480
470
465
468
452
466
7j

D.R. Patel, K.C. Patel / Dyes and Pigments 90 (2011) 1e10
7
0.9
1: Water
2: DMF
3: Methanol
1
0.8
4: Dichloro methane
5: Chloroform
1: Methanol
2: Methanol + KOH
3: Methanol + HCl
2
0.7
0.9
0.8
0.7
0.6
0.5
0.4
0.3
0.2
0.1
0.0
0.6
1
2
4
0.5
0.4
0.3
0.2
0.1
3
3
5
0.0
400
450
500
550
600
Wavelength (nm)
Fig. 3. Absorption spectra of dye 7f in acidic and basic solutions.
400
450
500
550
600
3.5.2. Dyeing of wool
Wavelength (nm)
Dye (0.2 g) was pasted with a few drops of cold water, then
about 80 ml cold water was added, and the mixture was stirred and
made up to 100 ml with dye solution (20 ml), acetic acid (1.5 ml of
10% v/v), glaubers’s salt solution (4 ml of 10% w/v) and water
(14.4 ml). A wool fabric (2 g) was introduced in to the dyebath at
30 ꢀC and the temperature was raised up to 40 ꢀC over 20 min.
Sulphuric acid (0.4 ml of 10% v/v) was then added and the dyeing
was continued for 40 min more at the same temperature. The
material was then removed, rinsed with cold water, soaping and
dried.
Fig. 1. Absorption spectra of dye 7a in various solvents.
components used, i.e. When H-acid used as coupling component, it
gives pink hues, J-acid gives yellow color hue and N-phenyl-j-acid
gives red color hue. A remarkable degree of levelness after washing
indicates good penetration and excellent affinity of these dyes with
silk, wool and cotton fibres.
3.5.1. Dyeing of silk
The dye (0.2 g) was pasted with a drop of cold water and then
about 80 ml of cold water was added and stirred well to give a clear
solution. The resulting dye solution was made up to 100 ml with the
dye solution (20 ml), acetic acid (2 ml of 10% v/v) and water 18 ml.
The dyebath temperature was maintained at 30 ꢀC and silk fabric
(2 g) was entered, and the temperature was raised to 40 ꢀC over
20 min. At this temperature formic acid (1.5 ml of 40% v/v) was
added to the dyebath to achieve good exhaustion. The dyeing was
continued for 40 min more and then the dyed material was washed
with cold water, soaping and dried.
3.5.3. Dyeing of cotton
Dye (0.2 g) was pasted with a few drops of cold water, then about
80 ml cold water was added, and the mixture was stirred and made
up to 100 ml with dye solution (20 ml), glaubers’s salt solution (4 ml
of 10% w/v) and water (14.4 ml). A cotton fabric (2 g) was introduced
in to the dyebath at 30 ꢀC and the temperature was raised up to
40 ꢀC over 20 min. Soda ash (Na2CO3) solution (0.4 ml of 10% v/v)
was then added to bring about fixation and the dyeing was
continued for 40 min more at the same temperature. The material
was then removed, rinsed with cold water, soaping and dried.
0.9
0.9
5
1
1: Water
2: DMF
3: Methanol
4: Dichloro methane
5: Chloroform
3
0.8
1: Chloroform
2: Chloroform + Piperidine
3: Dichloro methane
0.8
0.7
0.6
0.5
0.4
0.3
0.2
0.1
2
2
0.7
4
3
1
0.6
0.5
0.4
0.3
0.2
0.1
0.0
400
450
500
550
600
400
450
500
550
600
Wavelength (nm)
Wavelength (nm)
Fig. 2. Absorption spectra of dye 7f in various solvents.
Fig. 4. Absorption spectra of dye 7f in acidic and basic solutions.

8
D.R. Patel, K.C. Patel / Dyes and Pigments 90 (2011) 1e10
3.6. Exhaustion and fixation study
The color coordinates (Table 3) indicates that the dyes have good
affinity to silk, wool and cotton fibres.
The percentage dyebath exhaustion (%E) and percentage dye-
bath fixation (%F) of the dyed fabric were determined according to
known method [15].
The data summarized in Table 3 showed that, for silk fabric the
dyeing obtained using dye 7c was greener (as evidenced by the
lower a* value), duller (as shown by the lower C* value) and lighter
(as shown by the higher L* value) than the dye 7b. Similar result
was obtained by comparison of dye 7c with dye 7b. The dyeing
obtained by using dye 7h was greener, duller and darker than the
dye 7g, while the dye 7i was redder, duller and darker than the dye
7g. The color strength (K/S) values of all the dyes 7aej for silk fabric
followed the following order:
The percentage dyebath exhaustion of 2% dyeing ranges from 84
to 91% for silk, 84e90% for wool and 83e91% for cotton fibre. The
percentage dyebath fixation of 2% dyeing ranges from 74 to 81% for
silk, 75e83% for wool and 74e80% for cotton fibres. The exhaustion
is good for all the dyes 7aej, which shows good attachment of the
dye to the fibre. The presence of reactive group like s-triazine group
also improves the exhaustion and fixation value. The percentage
exhaustion and fixation data were summarized in Table 2.
7a > 7b > 7c > 7d > 7f > 7e > 7g > 7h > 7i > 7j
3.7. Fastness properties
Dye 7a having maximum value of color strength (K/S) while dye
7j having minimum value of color strength (K/S).
The light fastness, wash fastness and rubbing fastness properties
were assessed according to the standard method [16].
All the dyes 7aej show generally moderate to very good (3e6
value on grayscale) light fastness property and good to excellent
(3e5 value on grayscale) washing and rubbing fastness properties.
The results are given in Table 2 and they reveal that these dyes have
good fastness properties.
The higher values of rubbing fastness (Table 2) are associated
with higher molecular weights of the dyes, here dyes 7a, 7d and 7j
gave higher rubbing fastness properties than the other dyes
investigated.
From the data summarized in Table 3 showed that, for wool
fabric the dyeing obtained using dye 7c was greener, duller and
darker than dye 7b, while dye 7d was redder, duller and darker
than dye 7b. The K/S value of dyes 7aej for wool fabric followed the
following order:
7a > 7b > 7d > 7c > 7e > 7f > 7h > 7j > 7i > 7g
Here dye 7a having maximum value of K/S while dye 7g having
minimum value of K/S.
And finally for cotton fabric the data summarized in Table 3
showed that, the dye 7c was greener, duller and lighter than dye
7b while dye 7d was redder, duller and darker than dye 7b. Further
dye 7h was redder, brighter and darker than dye 7g. Similar results
can be obtained by comparing dyes 7i and 7g. The K/S value of dyes
7aej for cotton fabric followed the following order:
3.8. Color measurement
The color of a dyeing on silk, wool and cotton fibres are
expressed in terms of CIELAB values (Table 3) and the following
CIELAB coordinates were measured, Lightness (L*), chroma (C*),
hue angle form 0ꢀ to 360ꢀ (H), a* value represent the degree of
redness (positive) and greenness (negative) and b* represents the
degree of yellowness (positive) and blueness (negative). A reflec-
tance spectrophotometer was used for the colorimetric measure-
ments on the dyed samples. K/S values given by the reflectance
spectrophotometer are calculated at lmax and are directly corre-
lated with the dye concentration on the substrate according to the
KubelkaeMunk equation [17]:
7a > 7b > 7d > 7c > 7i > 7f > 7h > 7e > 7j > 7g
Dye 7a having highest K/S value while dye 7g having minimum
K/S value.
From the above data it is apparent that dye 7a having highest
K/S value on silk, wool and cotton fibres, showed that the dye 7a
having highest affinity for all these fabric.
K/S ¼ (1ꢂR)2/2R,
3.9. Antimicrobial activity
Where K e Absorbance coefficient, S e scattering coefficient and
R e reflectance ratio.
All the synthesized dyes (7aej) were tested for their antibacterial
and antifungal activity (MIC) in vitro by broth dilution method with
Table 2
%Exhaustion, %Fixation and fastness properties data of dyes 7a-j.
Dye No.
%Exhaustion
%Fixation
S
Light fastness
Wash fastness
Rubbing fastness
Dry
S
W
C
W
C
S
W
C
S
W
C
Wet
S
S
W
C
W
C
7a
7b
7c
7d
7e
7f
7g
7h
7i
89.15
90.13
90.60
88.15
87.63
86.75
85.10
86.08
85.35
84.92
89.58
88.06
85.53
87.23
87.55
88.13
85.55
84.13
86.20
87.10
90.25
88.35
85.15
84.13
86.25
87.65
84.48
83.76
84.16
86.63
80.20
78.78
78.92
76.00
75.89
76.10
76.38
74.93
74.98
74.18
82.61
80.07
77.76
76.81
75.39
77.73
77.15
76.08
78.88
79.22
79.78
78.01
76.34
74.29
76.52
77.58
74.58
74.63
75.46
79.08
4
5
6
5e6
5
6
5
4e5
4
6
3e4
3e4
6
3e4
4e5
5
4e5
4
3e4
3
3
4
3e4
4
4e5
5
4e5
4
3
4
4e5
3
4
4
4e5
4
4
3e4
3
4
3e4
4
5
4
3e4
5
3e4
4
3
3e4
4
5
4e5
4
5
3
3e4
4
4
3
4e5
4e5
4
3e4
4e5
3
3
3e4
3
5
4e5
4
4e5
3
3e4
3e4
4
5
4
4
5
3e4
3
3
3e4
4
4e5
4e5
3e4
3e4
5
4
3e4
3
4
4e5
4e5
4e5
4e5
5
3e4
4
6
4e5
6
4
4e5
3e4
6
3e4
4e5
5
3e4
5
3e4
5
7j
4e5
5
3e4
5
Abbreviations: S-Silk, W-Wool, C-Cotton.
Light fastness: 1-poor, 2-slight, 3-moderate, 4-fair, 5-good, 6-very good.
Wash & Rubbing fastness: 1-poor, 2-fair, 3-good, 4-very good, 5-excellent.

D.R. Patel, K.C. Patel / Dyes and Pigments 90 (2011) 1e10
9
Table 3
Colorimetric (CIELAB) data of dyes 7aej on silk, wool and cotton fibres.
Dye No.
L*
a*
b*
C*
H*
K/S
S
S
W
C
S
W
C
S
W
C
S
W
C
S
W
C
W
C
7a
7b
7c
7d
7e
7f
7g
7h
7i
45.41
60.86
68.41
71.21
78.23
72.32
83.64
83.21
79.54
85.37
32.36
53.40
51.36
43.45
55.38
50.73
69.92
64.20
67.97
57.70
42.05
64.17
64.30
51.39
67.14
63.97
79.22
73.65
69.89
73.23
54.18
39.06
29.46
22.51
13.63
22.62
05.71
05.01
14.48
02.13
49.00
38.02
35.65
39.93
34.92
35.27
13.67
23.17
16.54
31.55
54.00
36.56
34.05
38.83
26.11
29.60
13.83
16.04
17.45
12.80
06.36
49.14
33.98
14.56
14.94
15.34
21.36
18.38
12.34
14.02
17.38
51.80
45.64
32.38
45.42
29.64
27.70
44.98
30.90
24.46
11.48
50.52
38.06
31.06
25.24
24.38
27.32
35.04
29.22
20.62
54.55
62.78
44.98
26.81
20.22
27.33
22.11
19.05
19.02
14.18
51.99
64.26
57.91
51.41
57.29
46.07
30.89
50.60
35.05
39.92
55.21
62.36
51.07
49.72
36.31
38.35
30.62
38.54
34.03
24.27
06.70
51.52
49.07
32.90
47.63
34.15
75.04
74.77
40.44
81.34
19.53
53.72
52.01
39.04
52.44
40.04
63.73
62.75
61.85
37.78
12.00
54.11
48.19
38.66
44.03
39.48
63.15
65.41
59.16
58.18
10.76
07.65
02.52
00.91
00.47
00.84
00.43
00.41
00.40
00.33
26.18
14.35
13.26
14.12
08.75
06.34
02.05
04.33
02.83
03.44
13.30
06.20
03.74
07.02
01.60
01.97
00.89
01.86
02.51
01.31
7j
Abbreviations: S-Silk, W-Wool, C-Cotton
Table 4
Antibacterial and antifungal activity data of dyes 7aej.
Dye No.
Minimal bactericidal concentration (
Gram-negative
m
g/ml)
Minimal fungicidal concentration (mg/ml)
Gram-positive
E. coli
P. aeruginosa
S. aureus
S. pyogenes
C. albicans
A. niger
A. clavatus
MTCC443
MTCC 1688
MTCC 96
MTCC 442
MTCC 227
MTCC 282
MTCC 1323
7a
7b
7c
7d
7e
7f
7g
7h
62.5
500
100
500
250
62.5
500
1000
1000
500
100
50
200
500
200
1000
250
200
200
1000
1000
500
100
50
200
500
200
500
500
250
500
1000
1000
100
250
50
200
1000
200
500
500
500
1000
1000
500
1000
100
50
500
500
1000
100
1000
100
1000
100
500
1000
e
>1000
500
1000
250
1000
250
1000
250
>1000
500
>1000
250
>1000
250
1000
250
7i
7j
>1000
500
>1000
500
Ampicillin
Chloramphenicol
Nystatin
Greseofulvin
e
e
e
e
e
e
e
e
e
100
500
100
100
100
100
e
e
e
e
two Gram-positive bacteria S. aureus MTCC 96, Streptococcus pyo-
genes MTCC 442 and two Gram-negative bacteria Escherichia coli
MTCC443, Pseudomonas aeruginosa MTCC 1688 and fungi Candida
albicans MTCC 227, Aspergillus niger MTCC 282 and Aspergillus clav-
atus MTCC 1323 organism taking gentamycin, ampicillin, chloram-
phenicol, ciprofloxacin, norfloxacin, nystatin and greseofulvin as
standard drug. All MTCC cultures were collected from Institute of
Microbial Technology, Chandigarh and tested against known drugs
ampicillin and greseofulvin. MuellereHinton broth was used as
nutrient medium to grow and dilute the drug suspension for the test.
4. Conclusions
A series of monoazo reactive dyes based on 3-{4-[4-amino-2-
nitrobenzyl]-3-nitrophenyl}-7-chloro-2-phenylquinazolin-4(3H)-one
(3) have been prepared by conventional method in good yield. The
spectral properties, solvatochromic behavior, antimicrobial activity,
colorimetric data and their fastness properties have been evaluated.
Acknowledgements
The authors wish to thank the Professor and Head, Department
of Chemistry, VNSGU, Surat for providing laboratory facilities.
D. Rajani, Micro-care laboratory, Surat for antimicrobial activity,
S.A.I.F, Chandigarh for spectral data. Atul Ltd., Valsad for dyeing
facility and fastness test. One of the authors (Divyesh R. Patel) is
thankful to the Maa Foundation, Vapi for financial support.
3.9.1. Antibacterial activity
Dye 7a showed excellent activity against E. coli and very good
activity against S. aureus with respect to standard drug Ampicillin.
Dye 7j showed excellent activity against S. aureus with respect to
standard drug Ampicillin. Dye 7f showed excellent activity against
E. coli and equipotential activity against S. aureus with respect to
standard drug Ampicillin and dye 7c showed equipotential activity
against E. coli and very good activity against S. aureus with respect
to standard drug Ampicillin. Antibacterial activity data were
summarized in Table 4.
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