Synthesis of azoles based on N,N-bis(hydrazinocarbonyl-ethyl)-1,4- phenylenediamine

Article abstract of DOI:10.1007/s10593-009-0361-0

N,N-Bis[(1-methyl-3-oxobutylidene)hydrazinocarbonylethyl]-, N,N-bis[(2,5-dimethylpyrrol-1-yl)carbamoylethyl]-, N,N- bis(phenylureidocarbamoylethyl)-, N,N-bis(phenylcarbamoyl)-, N,N-bis(phenylureidocarbamoylethyl)-, and N,N-bis[(4,5-dihydro-5-oxo-4-phenyl-

Full text of DOI:10.1007/s10593-009-0361-0

Chemistry of Heterocyclic Compounds, Vol. 45, No. 7, 2009
SYNTHESIS OF AZOLES BASED
ON N,N'-BIS(HYDRAZINOCARBONYL-
ETHYL)-1,4-PHENYLENEDIAMINE
V. Novikovaite1 and Z. J. Beresnevičius1*
N,N'-Bis[(1-methyl-3-oxobutylidene)hydrazinocarbonylethyl]-, N,N'-bis[(2,5-dimethylpyrrol-1-yl)carba-
moylethyl]-, N,N'-bis(phenylureidocarbamoylethyl)-, N,N'-bis(phenylcarbamoyl)-, N,N'-bis(phenylureido-
carbamoylethyl)-, and N,N'-bis[(4,5-dihydro-5-oxo-4-phenyl-1,2,4-triazol-3-yl)ethyl]-1,4-phenylene-
diamines, and their thio analogs were obtained by the condensation of N,N'-bis-
(hydrazinocarbonylethyl)-1,4-phenylenediamine with 2,4-pentanedione, 2,5-hexanedione, phenyl
isocyanates, or phenyl isothiocyanates (with subsequent treatment of the obtained semicarbazides with
alkali), and carbon disulfide respectively.
Keywords: hydrazides, 1,3,4-oxadiazoles, pyrazoles, pyrroles, 1,2,4-triazoles, cyclization.
The chemical properties and biological activity of hydrazides and semicarbazides and also their
heterocyclization products are of interest to many investigators. In particular, certain derivatives of
semicarbazides exhibit antimicrobial activity [1, 2], and the triazole ring forms part of the structure of a series of
antimicrobial drugs [3]. With the aim of producing derivatives of substituted β-amino acids, which frequently
exhibit specific bioactivity [4-7], and continuing researches [8] into the synthesis of compounds each having two
heterocycles in their structure in the present work the azoles were synthesized, starting from N,N'-bis-
(hydrazinocarbonylethyl)-1,4-phenylenediamine.
The dihydrazide 2 was synthesized [9] by hydrazinolysis of N,N'-bis(methoxycarbonylethyl)-
1,4-phenylenediamine and also by the action of hydrazine under mild conditions on N,N'-diacetyl-N,N'-bis-
(methoxycarbonylethyl)-1,4-phenylenediamine, produced without isolation by the esterification of the diacid 1.
It is known [8] that derivatives of pyrazole are formed during the condensation of hydrazides with
2,4-pentanedione and dimethylpyrroles are formed in the reaction with 2,5-hexanedione. When the dihydrazide
2 is heated with acetylacetone in the presence of acetic or hydrochloric acids or without them tar formation is
observed, and it is not possible to isolate the individual substances. At room temperature, however, the
dihydrazone 3 is formed smoothly, but it was not possible to realize its cyclization to the pyrazole derivative 4.
_______
* To whom correspondence should be addressed, e-mail: zigmuntas.beresnevicius@ktu.lt.
1 Kaunas Technological University, Kaunas LT-50254, Lithuania.
__________________________________________________________________________________________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 998-1004, July, 2009. Original
article submitted July 8, 2008. Revision submitted April 25, 2009.
786
0009-3122/09/4507-0786©2009 Springer Science+Business Media, Inc.

Me
O
H
Me
N
N
O
N
N
N
Me
N
Me
N
4
H
O
Me
H
N
H
N
O
Me
N
Me
O
N
N
H
H
3
O
Me
OH
O
MeCOCH2COMe
Me
N
O
.
NH2NH2 H2O
O
N
Me
H
H
N
N
NH2
O
1
O
H2N
N
N
H
O
HO
H
2
MeCOCH2CH2COMe
O
Me
H
CS2, KOH
H
N
N
Me
N
N
O
N
H
N
H
Me
Me
5
S
H
N
N
O
HN
NH
O
N
N
H
S
6
The IR spectrum of the hydrazone 3 contains absorption bands for the amide and ketone carbonyl
1
groups at 1638 and 1625 cm−1, while the two nonequivalent methyl groups appear in the H NMR spectrum at
1.77 and 1.99 ppm. The reaction of the dihydrazide 2 with 2,5-hexanedione takes place readily, and the
1
derivative 5 is isolated from the reaction mixture with a yield of 75%. The H NMR spectrum of compound 5
contains signals for the methylene groups. The signals for the protons of the four methyl groups of the pyrrole
ring appear in the form of a singlet at 1.99 ppm, while the signals for the protons of the methine groups of the
pyrrole ring give a singlet at 5.64 ppm. In the IR spectrum the carbonyl groups absorb at 1664 cm−1. The bis
derivative of 2-thioxo-1,3,4-oxadiazole 6 was synthesized by boiling an alkaline solution of carbon disulfide in
alcohol with the hydrazide 2 followed by acidification of the obtained solution of the potassium salt of the
hydrazinecarbodithioate derivative with hydrochloric acid. In the 13C NMR spectrum of compound 6 the
sp2-hybridized carbon atoms of the C=N and C=S groups appear at 162.75 and 177.70 ppm respectively.
787

In order to obtain azoles containing phenyl substituents the hydrazide 2 was reacted with phenyl
isocyanates, and the diphenylcarbamoyl 7 or tetraphenylcarbamoyl 9 derivatives were obtained depending on
the ratio of the reactants. In the reaction of the dihydrazide with phenyl isothiocyanates the corresponding thio
analogs 8 and 10 were obtained.
R
X
H
H
N
N
O
H
H
N
N
N
N
H
H
O
N
N
H
H
X
R
7a,b, 8a,b
1. KOH
2. HCl
R
2
X
H
N
N
N
NH
X
HN
N
R
N
N
H
11a,b, 12a,b
R
1. KOH
2. HCl
R
H
N
H
N
O
X
N
N
X
H
N
H
N
X
H
N
H
N
X
4-ClC6H4NCS
N
O
H
R
N
H
R
9a,b, 10a,b
O
Cl
HN
N
N
S
N
H
N
S
N
H
N
N
N
NH
Cl
O
13
7, 9, 11 X = O; 8, 10, 12 X = S; 7–12 a R = H, b R = Cl
The oxotriazoles 11 and triazolethiones 12 were isolated by heating the phenylsemicarbazides 7 and
phenylthiosemicarbazides 8 with alkali and acidifying the reaction mixture. The cyclization of N,N'-bis-
(phenylcarbamoyl)-N,N'-bis(phenylureidocarbamoylethyl)-1,4-phenylenediamines 9 under the same conditions
788

is accompanied by removal of the phenylcarbamoyl group, and the same compounds 11 are produced. Similar
reactions occur when the thio derivatives 10 are heated, and under the same conditions give the phenyl-substituted
triazoles 12. The action of 4-chlorophenyl thioisocyanate on the triazole 12b in methanol gave N,N'-bis{[4,5-
dihydro-5-oxo-4-(4-chlorophenyl)-1,2,4-triazol-3-yl]ethyl}-N,N'-diphenylthiocarbamoyl-1,4-phenylenediamine
(13). The direction of thiocarbamoylation of compound (12b) is confirmed by the absence of a signal for the
hydrogen of the amine groups adjacent to the phenylene radical in the 1H NMR spectrum.
EXPERIMENTAL
The 1H and 13C NMR spectra were recorded on a Varian 300 instrument (300 and 75 MHz respectively)
in DMSO-d6 with TMS as internal standard. The IR spectra were recorded on a Perkin-Elmer Spectrum Bx
FT-IR spectrometer in tablets with KBr. The mass spectra were recorded on a Waters/Micromass ZQ 2000
instrument; chemoionization (ACPI+, 20 eV). Elemental analysis was performed on an Exeter Analytical
CE-440 Elemental instrument. The reaction and the purity of the obtained compounds were monitored by TLC
on Silufol 254 and Silufol UV-254 plates.
N,N'-Bis(hydrazinocarbonylethyl)-1,4-phenylenediamine (2). A. Sulfuric acid (1 ml) was added to a
solution of N,N'-diacetyl-N,N'-bis(ethoxycarbonyl)-1,4-phenylenediamine (1) (2 g, 6 mmol) in methanol
(20 ml), and the mixture boiled for 24 h. The reaction mixture was cooled, sodium carbonate was added, and the
mixture was filtered. The liquid fractions were distilled, hydrazine hydrate (0.6 g, 12 mmol) was added, and the
mixture was left at room temperature for 48 h. The crystals were filtered off and washed with diethyl ether. The
yield was 0.85 g (43%); mp 186.9-187.6°C (from 2-propanol).
B. From N,N'-bis(methoxycarbonylethyl)-1,4-phenylenediamine (5 g, 20 mmol) according to [9]
obtained 4.5 g (90%) of compound 2; mp 188-189°C. IR spectrum, ν, cm−1: 3126-3308 (NH, NH2), 3031 (CH
1
Аr), 2838-2946 (CH aliph.), 1643 (CO), 815 (p-substituted benzene). H NMR spectrum, δ, ppm (J, Hz): 2.27
(4H, t, J = 7.0, CH2CO); 3.14 (4H, t, J = 7.0, NHCH2); 4.20 (4H, br. s, NH2); 4.70 (2H, br. s, NH); 6.45 (4H, s,
H Ar); 9.03 (2H, s, NHNH2). Mass spectrum, m/z (Irel, %): 281 [M + H]+ (100).
N,N'-Bis[(1-methyl-3-oxobutylidene)hydrazinocarbonylethyl]-1,4-phenylenediamine (3). Acetyl-
acetone (1.6 g, 16 mmol) was added dropwise to a solution of the dihydrazide 2 (1.5 g, 5.4 mmol) in methanol
(20 ml). The mixture was stirred at 20°C for 24 h. The crystals that separated were filtered off and washed with
ether. The yield was 1.61 g (68%); mp 172-173°C (mixture of DMF and water). IR spectrum, ν, cm−1: 3384
(NH), 3312 (NH), 3034 (CH Аr), 2922-2952 (CH aliph.), 1638 (CO), 1625 (CO), 841 (p-substituted benzene).
1H NMR spectrum, δ, ppm (J, Hz): 1.77 (6H, s, CH3); 1.96 (6H, s, CH3); 2.74 (4H, t, J = 7.0, CH2CO); 3.18 (4H,
t, J = 7.0, NHCH2); 3.35 (4H, s, CH2C); 4.74 (2H, br. s, NH); 6.25 (2H, s, NHN=); 6.47 (4H, s, H Ar). Mass
spectrum, m/z (Irel, %): 467 [M + Na]+ (100). Found, %: C 59.85; H 7.40; N 19.01. C22H32N6O4. Calculated, %:
C 59.44; H 7.26; N 18.91.
N,N'-Bis[(2,5-dimethylpyrrol-1-yl)carbamoylethyl]-1,4-phenylenediamine (5).
A
mixture of
dihydrazide 2 (1 g, 3.6 mmol), 2-propanol (50 ml), 2,5-hexanedione (1 ml, 8 mmol), and acetic acid (1 ml) was
boiled for 3 h. The mixture was cooled, and the crystals that separated were filtered off. The yield was 1.17 g
(75%); mp 222-223°C (DMSO). IR spectrum, ν, cm−1: 3354 (NH), 3266 (NH), 3027 (CH Аr), 2836-2977 (CH
aliph.), 1664 (CO), 804 (p-substituted benzene). 1H NMR spectrum, δ, ppm: 1.99 (12H, s, CH3); 2.52-2.54 (4H,
m, CH2CO); 3.27-3.31 (4H, m, NHCH2); 4.84 (2H, br. s, NH); 5.64 (4H, s, CH); 6.52 (4H, s, H Ar); 10.62 (2H,
s, NH). Mass spectrum, m/z (Irel, %): 437 [M + H]+ (100). Found, %: C 65.76; H 7.34; N 18.99. C24H32N6O2.
Calculated, %: C 66.03; H 7.39; N 19.25.
N,N'-Bis[(2-thioxo-2,3-dihydro-1,3,4-oxadiazol-5-yl)ethyl]-1,4-phenylenediamine (6). To a solution
of KOH (1.68 g, 30 mmol) in ethanol (50 ml) we added dropwise CS2 (2.28 g, 30 mmol). The mixture was
stirred at room temperature for 15 min, a solution of dihydrazide 2 (2.8 g, 10 mmol) in ethanol (20 ml) was
789

added, and the mixture was boiled with stirring for 24 h. The liquid fractions were distilled, the remaining mass
was dissolved in water, and HCl was added to pH 5. The crystals that separated were filtered off and washed
with ether. The yield was 1.02 g (28%); mp 351-352°C (ethanol). IR spectrum, ν, cm−1: 3185 (NH), 3072 (CH
1
Аr), 2869 (CH aliph.), 1623 (C=N), 1163 (C=S), 818 (p-substituted benzene). H NMR spectrum, δ, ppm (J,
Hz): 2.93 (4H, t, J = 6.5, CH2CN); 3.33 (4H, t, J = 6.5, CH2NH); 6.50 (4H, s, H Ar); 8.56-9.50 (4H, m, NH). 13C
NMR spectrum, δ, ppm: 25.42; 40.50; 114.19; 139.55; 162.75; 177.70. Mass spectrum, m/z (Irel, %): 365 [M +
H]+ (70). Found, %: C 46.33; H 4.65; N 23.32. C14H16N6O2S2. Calculated, %: C 46.14; H 4.43; N 23.06.
N,N'-Bis(phenylureidocarbamoylethyl)-1,4-phenylenediamine (7a). A mixture of dihydrazide 2
(1.5 g, 5 mmol), phenyl isocyanate (1.5 g, 13 mmol), and methanol (10 ml) was kept at room temperature for
24 h, and the crystals that formed were filtered off. The yield was 1.1 g (40%); mp 155-156°C (ethanol).
1H NMR spectrum, δ, ppm (J, Hz): 2.28 (4H, t, J = 7.0, CH2CO); 3.15 (4H, t, J = 7.0, NHCH2); 4.26 (2H, br. s,
ArNH); 6.46 (4H, s, H Ar); 6.93-7.01 (2H, m, H Ar'); 7.22-7.28 (3H, m, H Ar'); 7.44-7.50 (5H, m, H Ar'); 8.04
(2H, s, NH); 8.72 (2H, s, NH); 9.04 (2H, s, NHAr). Mass spectrum, m/z (Irel, %): 519 [M + H]+ (80). Found, %:
C 60.68; H 5.40; N 21.99. C26H30N8O4. Calculated, %: C 60.22; H 5.83; N 21.61.
N,N'-Bis[(4-chlorophenyl)ureidocarbamoylethyl]-1,4-phenylenediamine (7b). From dihydrazide 2
(0.5 g, 1.8 mmol) and 4-chlorophenyl isocyanate (0.65 g. 4 mmol) by analogy with 7a we obtained 0.38 g (38%)
1
of compound 7b; mp 144-145°C (ethanol). H NMR spectrum, δ, ppm (J, Hz): 2.43 (4H, t, J = 6.6, CH2CO);
3.21 (4H, t, J = 6.6, NHCH2); 4.72 (2H, br. s, ArNH); 6.51 (4H, s, H Ar); 7.29-7.51 (8H, m, H Ar'); 8.13 (2H, d,
J = 10.0, NHNHCO); 8.89 (2H, d, J = 10.0, NHNHCO); 9.78 (2H, s, ArNH). Mass spectrum, m/z (Irel, %): 588
[M + H]+ (50). Found, %: C 53.68; H 4.40; N 19.31. C26H28Cl2N8O4. Calculated, %: C 53.16; H 4.80; N 19.07.
N,N'-Bis(phenylthioureidocarbamoylethyl)-1,4-phenylenediamine (8a). From dihydrazide 2 (1 g, 3.6
mmol) and phenyl isothiocyanate (1.2 g, 9 mmol) by analogy with compound 7a we obtained compound 8a with
1
a yield of 1.40 g (71%); mp 165-166°C (ethanol). H NMR spectrum, δ, ppm (J, Hz): 2.67 (4H, t, J = 6.6,
CH2CO); 3.33-3.36 (4H, m, NHCH2); 4.36 (2H, t, J = 6.6, ArNH); 6.55-7.53 (14H, m, H Ar + H Ar'); 9.63 (4H,
bs, NHNHCS); 10.02 (2H, br. s, NHAr). Mass spectrum, m/z (Irel, %): 552 [M + H]+ (100). Found, %: C 56.98;
H 5.40; N 20.21. C26H30N8O2S2. Calculated, %: C 56.71; H 5.49; N 20.35.
N,N'-Bis(phenylcarbamoyl)-N,N'-bis(phenylureidocarbamoylethyl)-1,4-phenylenediamine (9a). A
mixture of dihydrazide 2 (1 g, 3 mmol) and phenyl isocyanate (2.1 ml, 18 mmol) in methanol (20 ml) was kept
at room temperature for 24 h. The crystals that separated were filtered off and washed with methanol. The yield
1
was 0.6 g (22%); mp 170-171°C (mixture of DMF and water). H NMR spectrum, δ, ppm (J, Hz): 2.52-2.57
(4H, m, CH2CO); 3.98 (4H, t, J = 7.2, NHCH2); 6.94-7.01 (4H, m, H Ar'); 7.22-7.28 (8H, m, H Ar'); 7.45-7.47
(8H, m, H Ar'); 7.50 (4H, s, H Ar); 7.87 (2H, br. s, NHNHCO); 8.06 (2H, br. s, NHNHCO); 8.76 (2H, s, NHAr);
9.83 (2H, s, NHAr). Mass spectrum, m/z (Irel, %): 758 [M + H]+ (50). Found, %: C 63.98; H 5.30; N 18.31.
C40H40N10O6. Calculated, %: C 63.48; H 5.33; N 18.51.
N,N'-Bis[(4-chorophenyl)carbamoyl]-N,N'-bis[(4-chlorophenyl)ureidocarbamoylethyl]-1,4-phenylene-
diamine (9b). From dihydrazide 2 (0.5 g, 1.8 mmol) and 4-chlorophenyl isocyanate (1.5 g, 10 mmol) in
methanol (10 ml) by analogy with the synthesis of compound 9a we obtained 0.25 g (16%) of compound 9b; mp
1
211-212°C (mixture of DMF and water). H NMR spectrum, δ, ppm (J, Hz): 2.52-2.56 (4H, m, CH2CO); 3.97
(4H, t, J = 6.3, NHCH2); 7.28-7.34 (8H, m, H Ar'); 7.47-7.50 (12H, m, H Ar + H Ar'); 7.96 (2H, br. s,
NHNHCO); 8.13 (2H, br. s, NHNHCO); 8.86 (2H, s, NHAr); 9.83 (2H, s, NHAr). Mass spectrum, m/z (Irel, %):
895 [M + H]+ (50). Found, %: C 53.98; H 4.40; N 15.31. C40H36Cl4N10O6. Calculated, %: C 53.70; H 4.06;
N 15.66.
N,N'-Bis(phenylthiocarbamoyl)-N,N'-bis(phenylthioureidocarbamoylethyl)-1,4-phenylenediamine
(10a). From dihydrazide 2 (1 g, 3.6 mmol) and phenyl isocyanate (3 g, 22 mmol) in methanol (20 ml) after
stirring the reaction mixture at room temperature for 24 h by analogy with compound 9a we obtained 1.15 g
1
(39%) of compound 10a; mp 157-158°C (mixture of DMF and water). H NMR spectrum, δ, ppm (J, Hz):
2.52-2.57 (4H, m, CH2CO); 3.98 (4H, t, J = 6.9, NHCH2); 6.94-7.01 (4H, m, H Ar'); 7.25 (8H, t, J = 7.5,
790

H Ar'); 7.46 (8H, d, J = 7.5, H Ar'); 7.51 (4H, s, H Ar); 7.86 (2H, br. s, NHNHCO); 8.05 (2H, br. s, NHNHCO);
8.73 (2H, s, NHAr); 9.83 (2H, s, NHAr). Mass spectrum, m/z (Irel, %): 822 [M + H]+ (60). Found, %: C 58.98;
H 4.44; N 17.31. C40H40N10O2S4. Calculated, %: C 58.51; H 4.91; N 17.06.
N,N'-Bis[(5-oxo-4-phenyl-4,5-dihydro-1,2,4-triazol-3-yl)ethyl]-1,4-phenylenediamine (11a). A.
Compound 7a (0.55 g, 1 mmol) was boiled in 10% KOH (15 ml) for 4 h. The mixture was cooled, 18% HCl was
added to pH 4, and the precipitate that separated was filtered off, washed with water, and crystallized from a
1:10 mixture of DMF and water. We obtained 0.25 g (49%) of compound 11a; mp 195-196°C.
B. Compound 9a (0.75 g, 1 mmol) was boiled in 15 ml of a 10% solution of KOH for 4 h. The product
was isolated by analogy with method A. The yield was 0.32 g (67%); mp 197-198°C. 1H NMR spectrum, δ, ppm
(J, Hz): 2.60 (4H, t, J = 7.3, NHCH2CH2); 3.08 (4H, t, J = 7.3, NHCH2); 4.85 (2H, br. s, ArNH); 6.19 (4H, s,
H Ar); 7.40–7.58 (10H, m, H Ar'); 11.72 (2H, s, NHN). Mass spectrum, m/z (Irel, %): 505 [M + Na] (50). Found,
%: C 64.98; H 5.50; N 23.31. C26H26N8O2. Calculated, %: C 64.72; H 5.43; N 23.22.
N,N'-Bis{[4-(4-chlorophenyl)-5-oxo-4,5-dihydro-1,2,4-triazol-3-yl]ethyl}-1,4-phenylenediamine (11b).
A. From compound 7b (0.7 g, 1.2 mmol) by boiling in 10% KOH (20 ml) by analogy with compound 11a we
obtained 0.22 g (33%) of compound 11b; mp 187-188°C (mixture of DMF and water).
B. From compound (9b) (0.67 g, 0.75 mmol) by analogy with method B we obtained 0.22 g (52%) of
compound 11b; mp 188-189°C. 1H NMR spectrum, δ, ppm (J, Hz): 2.61 (4H, t, J = 7.4, NHCH2CH2); 3.09 (4H,
t, J = 7.4, NHCH2); 4.86 (2H, br. s, ArNH); 6.19 (4H, s, H Ar); 7.47 (4H, d, J = 8.6, H Ar'); 7.60 (4H, d, J = 8.6,
H Ar'); 11.75 (2H, s, NHN). Mass spectrum, m/z (Irel, %): 552 [M + H]+ (60). Found, %: C 56.60; H 4.40;
N 20.31. C26H24Cl2N8O2. Calculated, %: C 56.63; H 4.39; N 20.32.
N,N'-Bis[(4-phenyl-5-thioxo-4,5-dihydro-1,2,4-triazol-3-yl)ethyl]-1,4-phenylenediamine (12a). A.
From compound 8a (0.55, 1.2 mmol) by boiling in 10 ml of 10% KOH for 3 h by analogy with compound 11a
we obtained 0.27 g (53%) of compound 12a; mp 219-220°C (mixture of DMF and water).
B. From compound 10a (1 g, 1.2 mmol) by boiling for 4 h in 10% KOH (20 ml) by analogy with
compound 11a we obtained 0.58 g (92%) of compound 12a; mp 219-220°C. 1H NMR spectrum, δ, ppm (J, Hz):
2.63 (4H, t, J = 7.0, NHCH2CH2); 3.11 (4H, t, J = 7.0, NHCH2); 4.88 (2H, br. s, ArNH); 6.17 (4H, br. s, H Ar);
7.42-7.58 (10H, m, H Ar'); 13.67 (2H, s, NHN). Mass spectrum, m/z (Irel, %): 516 [M + H]+ (50). Found, %:
C 60.75; H 5.40; N 21.31. C26H26N8S2. Calculated, %: C 60.68; H 5.09; N 21.77.
N,N'-Bis{[4-(4-chlorophenyl)-5-oxo-4,5-dihydro-1,2,4-triazol-3-yl]ethyl}-N,N'-bis(phenylthiocarbamo-
yl)-1,4-phenylenediamine (13). A mixture of triazole 11b (0.2 g, 40 mmol), phenyl isothiocyanate (0.2 g,
1.5 mmol), and methanol (5 ml) was kept at 20°C for 24 h. The crystals that separated were filtered off and
1
washed with ethanol. The yield was 0.21 g (70%); mp 245-246°C (mixture of DMF and water). H NMR
spectrum, δ, ppm (J, Hz): 2.90 (4H, t, J = 7.3, NHCH2CH2); 4.31 (4H, t, J = 7.3, NCH2); 7.14-7.59 (22H, m,
H Ar + H Ar'); 8.37 (2H, s, NHAr); 11.80 (2H, s, NHN). Mass spectrum, m/z (Irel, %): 823 [M + H]+ (50).
Found, %: C 58.60; H 4.40; N 17.31. C40H34Cl2O2S2. Calculated, %: C 58.46; H 4.17; N 17.04.
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