Condensation of o-phenylenediamine with cinnamic acids

Article abstract of DOI:10.1081/SCC-100106202

Condensation of o-phenylenediamine sulfate with cinnamic acids in refluxing ethylene glycol yielded the corresponding 2-styrylbenzimidazoles in excellent yields.

Full text of DOI:10.1081/SCC-100106202

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CONDENSATION OF O-PHENYLENEDIAMINE WITH
CINNAMIC ACIDS
P. K. Dubey a , Ramesh Kumar a , C. Ravi Kumar a , J. S. Grossert b & D. L. Hooper b
a Department of Chemistry, College of Engineering, J. N. T. University, Kukatpally,
Hyderabad, 500 072, India
b Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H4J3, Canada
Published online: 22 Aug 2006.
To cite this article: P. K. Dubey , Ramesh Kumar , C. Ravi Kumar , J. S. Grossert & D. L. Hooper (2001) CONDENSATION
OF O-PHENYLENEDIAMINE WITH CINNAMIC ACIDS, Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, 31:22, 3439-3446, DOI: 10.1081/SCC-100106202
To link to this article: http://dx.doi.org/10.1081/SCC-100106202
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SYNTHETIC COMMUNICATIONS, 31(22), 3439–3446 (2001)
CONDENSATION OF
o-PHENYLENEDIAMINE
WITH CINNAMIC ACIDS
P. K. Dubey,1, Ramesh Kumar,1
*
C. Ravi Kumar,1 J. S. Grossert,2
and D. L. Hooper 2
1Department of Chemistry, College of Engineering,
J. N. T. University, Kukatpally,
Hyderabad – 500 072, India
2Department of Chemistry, Dalhousie University,
Halifax, Nova Scotia B3H4J3, Canada
ABSTRACT
Condensation of o-phenylenediamine sulfate with cinnamic
acids in refluxing ethylene glycol yielded the corresponding
2-styrylbenzimidazoles in excellent yields.
INTRODUCTION
In an earlier communication,1 we have reportedthe preparation of
2-styrylbenzimidazoles by condensation of 2-methyl/ethylbenzimidazoles
with aromatic aldehydes. Literature survey revealed that o-phenylenedia-
mine condenses with aliphatic acids in aq. HCl (Phillips conditions)2 and
*Corresponding author.
3439
Copyright & 2001 by Marcel Dekker, Inc.
www.dekker.com

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DUBEY ET AL.
with aromatic acids in PPA3 or PPE4 at 180–200ꢀC, andit appears that
there is no standard method for the condensation of unsaturated acids with
o-phenylenediamine. Hence, it was considered worthwhile to develop a
simple andefficient methodfor the condensation of o-phenylenediamine
with unsaturatedacids, which forms the subject matter of this paper.
RESULTS AND DISCUSSION
Attemptedconednsation of
o-phenylenediamine (1) with cinnamic
acidin refluxing methanol containing a trace of sulfuric acidor in refluxing
benzene with a trace of p-toluenesulphonic acid, and removal of water by
the Dean–Stark apparatus ledto the recovery of starting materials.
ꢀ
However, condensation of 1 with cinnamic acidin PPA at 200 C, yielded
2-styrylbenzimidazole (2a) in 30% yield.
Nagarajan has reportedthe synthesis of 2a in 57% yieldby condensa-
tion of o-phenylenediamine dihydrochloride with cinnamic acid at 200ꢀC,
for 2 h.5 Treatment of 1 with cinnamic acid under Phillips’ conditions led to
the recovery of starting materials.
In the present work, condensation of o-phenylenediamine sulfate
(1.H2SO4) with cinnamic acidin refluxing ethylene glycol for 3 h followed
by simple processing yielded 2a in 95% yield. This condensation of
1.H2SO4, with cinnamic acidhas been extendedto fourteen more cinnamic
acids to obtain the corresponding 2-styrylbenzimidazoles in excellent yields.
The results are shown in the Table. The authenticity of 2a–2f and 3a–3f was
confirmedby comparison of mp, mmp, tlc andIR spectra with those of the
products obtained by condensation of 2-methyl/ethylbenzimidazoles with
aromatic aldehydes as reported earlier. 1The structures 4,5 and 6 are
assignedbasedon their spectral andanalytical data.
This appears to be a general methodandmay be appliedfor the
preparation of other benzimidazole derivatives with unsaturated moiety in
2–position, which are difficult to obtain by other known methods. Thus,
compounds 5 and 6, which cannot be preparedby the condensation of

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o-PHENYLENEDIAMINE
3441
Table. Condensation of 1.H2SO4 with Cinnamic Acids to Obtain 2,3,4,5 and 6
Product obtained
YieldRexn.
(%)
M.P.
0
Cinnamic acidused
Cinnamic acid
R
R
R00
H
solvent
(ꢀC)
2a
H
H
95
Aq. CH3OH
203–05
(Lit11 m.p.
¼ 201–02)
214–16
p-Methylcinnamic acid 2b
o-Chlorocinnamic acid 2c
p-Chlorocinnamic acid 2d
H
H
H
4-CH3
2-Cl
4-Cl
H
H
H
92
99
96
Aq. CH3OH
Aq. CH3OH
Aq. CH3OH
176–78
221–23
(Lit12 m.p. ¼
223–224)
m-Nitrocinnamic acid
p-Nitrocinnamic acid
2e
2f
H
H
H
3-NO2
4-NO2
H
H
H
97
96
91
EtOH + Hexane 219–20
AcOH
CH3OH
260–62
242–44
(Lit13 m.p. ¼
245)
a-Methylcinnamic acid 3a
CH3
p-Methyl-a-
methylcinnamic acid
3b
3c
3d
3e
3f
H
H
H
H
H
4-CH3 CH3
94
95
97
93
98
EtOAc
178–80
o-Chloro-a-
2-Cl
4-Cl
CH3
CH3
Aq. CH3OH
Aq. CH3OH
Aq. CH3OH
Aq. CH3OH
264–65
223–25
231–33
294–95
methylcinnamic acid
p-Chloro-a-
methylcinnamic acid
m-Nitro-a-
methylcinnamic acid
p-Nitro-a-
3-NO2 CH3
4-NO2 CH3
methylcinnamic acid
a-Phenylcinnamic acid
b-Methylcinnamic acid
b-Phenylcinnamic acid
4
5
6
H
H
H
H
C6H5
H
92
90
94
Aq. CH3OH
Aq. CH3OH
281–83
195–96
CH3
C6H5
H
EtOAc þ Hexane 102–04
2-methylbenzimidazole with acetophenone and benzophenone respectively
can be preparedby this method.
EXPERIMENTAL
All melting points are uncorrectedandwere obtainedusing open
capillary tubes in sulfuric acidbath. TLC analysis was carriedout on
glass plates coatedwith silica gel-G, andspots were visualizedusing
iodine or a UV Lamp. IR spectra were recorded using Perkin–Elmer
1
Model 46 instrument in KBr discs. H-NMR and 13C-NMR spectra were
recorded on a Bruker instrument operating at 250 MHz and 62.9 MHz

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DUBEY ET AL.
respectively. Mass spectra were recorded on a CEC-21-110 mass spectro-
meter under electron impact conditions.
Preparation of 1.H2SO4
To a solution of 1 (5.4 gms, 50 mM) in methanol (50 ml), conc. H2SO4
(4 ml) was added, drop wise under ice-cold conditions over a period of
30 min. After the completion of addition, the separated product was filtered,
washed with methanol and dried. Yield ¼ 7.21 gms (70%) (Anal. Calcdfor
C6H10N2O4S: %C, 30.762; %H, 4.301; %N, 13.561; Found: %C, 30.760;
%H, 4.299; %N, 13.560).
Condensation of 1.H2SO4 with Cinnamic Acids6^10
to Obtain 2,3,4,5 and 6
A mixture of 1.H2SO4 (2.06 g, 10 mM) andsubstitutedcinnamic acid
(10 mM) in ethylene glycol (10 ml) was refluxedfor 3 h. Then, the reaction
mixture was cooledto RT andpouredinto water (100 ml). The pH of the
solution was adjusted to >7 with NaHCO3. The product was filtered,
washed, dried and recrystallized to obtain 2,3,4,5 and 6.
Spectral Data of Compounds 2a–6
1
2a H-NMR (CDCl3/TMS): d 7.2–7.8 (complex m, 11H, five phenyl
3
protons, four aryl protons andtwo vinylic protons, JH-H for vinylic system
¼ 16.5 Hz), 12.04 (1H, NH); 13C-NMR (CDCl3/TMS): d 114.93, 117.10,
122.61, 126.93, 128.76, 128.82, 135.36, 135.79, 139.23, 151.65 (for all
carbons of 2-styrylbenzimidazole); MS: m/z (%I): 221 (6, M þ 1), 220
(40, Mþ), 219 (100, Mꢁ1), 218 (12, Mꢁ2), 110 (8), 109 (12), 108 (4), 92
(4), 91 (6), 77 (3), 51 (2) etc. (Anal. Calcdfor C 15H12N2: %C, 81.791; %H,
5.490; %N, 12.717; Found: %C, 81.789; %H, 5.488; %N, 12.71).
1
2b H-NMR (CDCl3/TMS): d 2.31 (s, 3H, CH3), 7.12–7.66 (complex
m, 10H, four p-methyl phenyl protons, four aryl protons andtwo vinylic
3
protons, JH-H ¼ 16.63 Hz). 13C-NMR (CDCl3/TMS): d 20.97 (CH3),
116.68, 122.02, 126.99, 129.60, 133.02, 134.32, 138.53, 151.12 (six p-methyl-
phenyl carbons, one imidazole quaternary carbon and two vinylic carbons);
MS: m/z (%I): 235 (6.6, M þ 1), 234 (41.7, Mþ), 233 (100, Mꢁ1), 232 (10.2),
116 (12), 103 (3.7), 92 (1.2), 91 (1.9), 90 (1.2), 78 (2.7), 77 (2.3), 65 (2.3) etc.

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3443
(Anal. Calcdfor C 16H14N2: %C, 82.020; %H, 6.022; %N, 11.952; Found:
%C, 82.019; %H, 6.020; %N, 11.950).
1
2c H-NMR (CDCl3/TMS): d 7.2–7.7 Complex m, 9H, four o-chlor-
ophenyl protons, four aryl protons andone vinylic proton a-to heteryl ring),
7.88 (d, 1H, vinyþlic proton b-to heteryl ring); MS: m/z (%I): 254 and256
(13.4 and1.5, M corresponding to 35Cl and 37Cl), 253 and255 (14.9 and
4.47, Mꢁ1), 220 (13.4), 219 (100, M-Cl), 218 (20.9), 129 (5.2), 77 (7.5), 65
(8.95), 64 (16.4) etc. (Anal. Calcdfor C 15H11N2Cl: %C, 70.731; %H, 4.352;
%N, 10.997; Found: %C, 70.730; %H, 4.351; %N, 10.995).
2d 1H-NMR (CDCl3/TMS): d 7.14–7.72 (Complex m, 10H, four
p-chlorophenyl protons, four aryl protons andtwo vinylic protons), 12.7
(bs, 1H, -NH); 13C-NMR (CDCl3/TMS): d 111.19, 118.55, 122.16, 128.72,
128.98, 132.92, 133.20, 134.74, 151.56, (six p-chlorophenyl carbons, six aryl
carbons, one imidazole quaternary carbon and two vinylic carbons) etc;
MS: m/z (%I): 256, 254 (14.3, 42.9; M þ 2, Mþ) 255, 253 (39.3, 100;
[(M þ 2)-1, Mꢁ1]), 219 (6), 218 (8), 109 (8.6). (Anal. Calcdfor
C15H11N2Cl: %C, 70.731; %H, 4.352; %N, 10.997; Found: %C, 70.730;
%H, 4.351; %N, 10.995).
2e 1H-NMR (CDCl3/TMS): d 7.1–8.2 (Complex m, 10H, four m-nitro-
phenyl protons, four aryl protons andtwo vinylic protons); MS: m/z (%I):
266 (6.63, M þ 1), 265 (55, Mþ), 264 (100, Mꢁ1), 236 (6.73), 235 (20.78),
234 (34.54), 219 (10.73), 218 (30.8), 217 (16.25), 43 (10.16), 42 (9.74);
HRMS: calculatedfor C 15H11N3Oþ2 ¼ 265.085 amu; found ¼ 265.0859 þ /
ꢁ0.0008 amu. (Anal. Calcdfor C 15H11N2O2: %C, 67.917; %H, 4.179;
%N, 15.840; Found: %C, 67.916; %H, 4.178; %N, 15.839).
1
2f H-NMR (CDCl3/TMS): d 7.21 and7.50 (complex m, 4H, aryl
protons), 7.40, 7.56, 7.72 and7.78 (AB quartet, 2H, vinylic protons, JH-H
3
¼ 16.55 Hz), 7.89, 7.93, 8.22 and8.25 (A 2B2 quartet, 4H, p-nitrophenyl
protons, Jortho ¼ 8.2 Hz); 13C-NMR (CDCl3/TMS): d 115.13, 122.06,
122.57, 124.16, 128.00, 131.90, 142.46, 146.92 and150.60 (six p-nitrophenyl
carbons, six aryl carbons, one imidazole quaternary carbon and two vinylic
carbons); MS: m/z (%I): 266 (10, M þ 1), 265 (55, Mþ), 264 (100, Mꢁ1),
234 (10), 219 (21), 218 (67), 217 (30), 206 (8). (Anal. Calcdfor C 15H11N3O2:
%C, 67.917; %H, 4.179; %N, 15.840; Found: %C, 67.916; %H, 4.178;
%N, 15.839).
1
3a H-NMR (CDCl3/TMS): d 7.12–7.49 (complex m, 9H, four aryl
andfive phenyl protons), 7.57 (s, 1H, vinylic proton), 12.58 (s, 1H, -NH);
13C-NMR (CDCl3/TMS): d 15.30 (CH3), 122.00, 127.51, 127.59, 128.55,
129.32, 130.26, 136.52 and154.00 (six phenyl carbons, six aryl carbons,
one imidazole quaternary carbon and two vinylic carbons); MS: m/z
(%I): 236 (0.14, M þ 2), 235 (2.30, M þ 1), 234 (56.9, Mþ), 233 (100,
Mꢁ1), 232 (10.2), 219 (8.44), 157 (44.32), 155 (8.36), 141 (5.34), 129

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DUBEY ET AL.
(12.7), 127 (10þ.42) and117 (2.85); HRMS: found ¼ 233.1079 amu; calculated
for C16H13N2 (Mꢁ1) is 233.1079 amu. (Anal. Calcdfor C 16H14N2: %C,
82.020; %H, 6.022; %N, 11.956; Found: %C, 82.019; %H, 6.021;
%N, 11.954).
1
3b H-NMR (CDCl3/TMS): d 2.35–2.45 (two singlets, 6H, 2 ꢂ CH3),
7.1–7.8 (complex, 9H, four p-methylphenyl protons, four aryl protons
andone vinylic protons), 12.6 (s, 1H, -NH); 13C-NMR (CDCl3/TMS): d
20.27 (Phenyl CH3), 15.30 (allylic CH3), 111.01, 118.73, 121.08, 121.37,
122.48, 126.76, 129.16, 129.31, 130.25, 133.68, 134.96, 136.98, 143.60,
154.17 (six p-methylphenyl carbons, six aryl carbons, one quaternary imi-
dazole carbon and two vinylic cabons); MS: m/z (%I): 249 (2, M þ 1), 248
(19, Mþ), 247 (100, M ꢁ 1), 246 (3), 245 (1), 234 (2), 233 (3), 232 (2), 128
(0.7), 116 (07); HRMS calcdfor C 17H15Nþ2 (M ꢁ 1) ¼ 247.1235 amu;
found ¼ 247.1236 amu. (Anal. Calcdfor C 17H16N2: %C, 82.222; %H,
6.494; %N, 11.280; Found: %C, 82.221; %H, 4.493; %N, 11.278).
1
3c H-NMR (CDCl3/TMS): d 2.36 (s, 3H, CH3), 7.16–7.62 (complex
m, 9H, four o-chlorophenyl protons, four aryl protoþns andone vinylic
proton); MS: m/z (%I): 268 and270 (2.23 and3, M
corresponding to
35Cl and 37Cl), 267 and269 (18.6 and4.47, M ꢁ1), 234 (14.18), 233 (100,
M ꢁ C1), 232 (10.45), 116 (6.95), 115 (14.92), 66 (10.44), 65 (9.7), 64 (14.92)
etc. (Anal. Calcdfor C 16H13N2Cl: %C, 71.508; %H, 4.875; %N, 10.423;
Found: %C, 71.506; %H, 4.873; %N, 10.421).
1
3d H-NMR (CDCl3/TMS): d 2.45 (s, 3H, CH3), 7.1–7.8 (complex m,
9H, four p-chlorophenyl protons, four aryl protons andone vinylic proton),
12.7 (s, 1H, NH);13C-NMR (CDCl3/TMS): d 15.25 (CH3), 111.11, 118.85,
121.51, 122.67, 128.37, 128.57, 128.93, 131.05, 132.03, 134.94, 135.37,
143.56, 153.75 (six p-chlorophenyl carbons, six aryl carbons, one imidazole
quaternary carbon andtwo vinylic carbons); MS: m/z (%I): 268 and270
(insignificant intensity, twin peaks, Mþ corresponding to 35Cl and 37Cl), 267
and269 (M ꢁ 1 corresponding to 35Cl and 37Cl). (Anal. Calcdfor
C16H13N2Cl: %C, 71.508; %H, 4.875; %N, 10.423; Found: %C, 71.506;
%H, 4.873; %N, 10.421).
1
3e H-NMR (CDCl3/TMS): d 2.51 (s, 3H, CH3), 7.27–8.22 (complex
m, 8H, four m-nitrophenyl protons andfour aryl protons), 8.3 (s, 1H, vinylic
proton); MS: m/z (%I): 279 (23.9, Mþ), 278 (100, M ꢁ 1), 248 (26.86), 233
(17.9), 232 (67.1), 231 (35.8), 218 (17.9), 140 (7.46), 115 (20.9), 103 (10.44),
102 (9.7), 78 (24.6), 76 (12.7), 66 (32), 65 (19.4), 64 (32) etc. (Anal. Calcdfor
C16H13N2O2: %C, 68.800; %H, 4.691; %N, 15.045; Found: %C, 68.800;
%H, 4.690; %N, 15.044).
1
3f H-NMR (CDCl3/TMS): d 2.45 (s, 3H, CH3), 7.1–8.4 (complex m,
9H, four p-nitrophenyl protons, four aryl protons andone vinylic proton);
13C-NMR (CDCl3/TMS): d 15.5 (3), 122.35, 123.642, 128.134, 130.282,

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o-PHENYLENEDIAMINE
3445
131.292, 143.335, 145.955, 153.229 (six p-nitrophenyl carbons, six aryl
carbons, two vinylic carbons andone imidazole quaternary carbon); MS:
m/z (%I): 279 (32.8, Mþ), 278 (100, Mꢁ1), 249 (10.4), 248 (41.8), 233 (35.8),
232 (91), 231 (40.3), 218 (16.4), 190 (23.9), 145 (7.46), 131 (10.44), 116 (46.2),
115 (58.2), 77 (41.8), 65 (25.4), 64 (14.9), 63 (34.32) etc. (Anal. Calcdfor
C16H13N3O2: %C, 68.800; %H, 4.691; %N, 15.045; Found: %C, 68.800;
%H, 4.690; %N, 15.044).
1
4 H-NMR (DMSO-d6): d 7.11–7.50 (complex m, 14H, ten phenyl
protons andfour aryl protons), 8.12 (sharp s, 1H, vinylic proton); MS:
m/z (%I): 296 (100, Mþ), 219 (41.2), 218 (18), 181 (10), 178 (11.1), 176
(8.9), 169 (10), 148 (14.7), 147 (14.9), 146 (15), 131 (25), 119 (25), 92 (5.9),
77 (19.1), 69 (90), 65 (14.9), 64 (10), 63 (14), 51 (34), 44 (54.4). (Anal. Calcd
for C21H16N2: %C, 85.106; %H, 5.441; %N, 9.452; Found: %C, 85.105;
%H, 5.440; %N, 9.450).
1
5 H-NMR (CDCl3/TMS): d 2.8 (s, 3H, CH3), 6.82 (s, 1H, vinylic
proton), 7.26–7.72 (complex m, 9H, five phenyl andfour aryl protons),
12.4 (broads, 1H, -NH); 13C-NMR (CDCl3/TMS): d 17.93 (CH3),
115.124, 121.996, 125.86, 128.146, 128.633, 142.532, 144.088, 150.998 (six
phenyl carbons, six aryl carbons, two vinylic carbons andone imidazole
quaternary carbon); MS: m/z (%I): 236 (4.2, M þ 2), 235 (22.8, M þ 1),
234 (46, Mþ), 233 (100, M ꢁ1), 231 (4.6), 219 (8.85), 218 (7), 156 (4), 131
(3.5), 128 (3.5), 117 (3.5), 116 (8.85), 115 (10.6), 109 (4), 105 (4.4), 104 (5.3),
103 (8), 102 (4.4), 92 (4.4), 91 (6.2), 90 (3.5). (Anal. Calcdfor C 16H14N2:
%C, 82.0220; %H, 6.022; %N, 11.956; Found: %C, 82.019; %H, 6.020;
%N, 11.952).
6 1H-NMR (CDCl3/TMS): d 7.1–7.7 (complex m, ten phenyl protons,
four aryl protons andvinylic proton); 13C-NMR (CDCl3/TMS): d 117.327,
122.896, 127.316, 128.57, 128.71, 129.043, 129.662, 129.76, 139.00, 140.5,
146.4 and150.00 (twelve phenyl carbons, six aryl carbons, two vinylic
carbons andone imidazole quaternary carbon); MS: m/z (%I): 298 (3.7,
M þ 2), 297 (17.7, M þ 1), 296 (29.7, Mþ), 295 (100, M ꢁ1), 293 (7.1), 219
(9.7), 218 (4.9), 147 (10.6), 105 (2.6), 91 (3.1), (Anal. Calcdfor C 21H16N2:
%C, 85.106; %H, 5.441; %N, 9.452; Found: %C, 85.105; %H, 5.440;
%N, 9.450).
ACKNOWLEDGMENT
The authors are grateful to UGC, New Delhi, India and NSERC,
Ottawa, Canada for financial support. They are also thankful to Dr. K.
Syamasunder, Professor and Head, Department of Chemistry, J. N. T.

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DUBEY ET AL.
University, Hyderabad for providing laboratory facilities and constant
encouragement.
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^
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`
Chem. Abstr. 1938, 32, 2251.
Receivedin the UK November 9, 1999

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