Reactions of N-(2,2,2-trichloroethylidene)- and N-(2,2-dichloro-2- phenylethylidene)arenesulfonamides with biuret

Article abstract of DOI:10.1134/S1070428008100138

N-(2,2,2-Trichloroethylidene)- and N-(2,2-dichloro-2-phenylethylidene) arenesulfonamides react with an equimolar amount of biuret to give 1-(1-arylsulfonylamino-2,2,2-trichloroethyl)- or 1-(1-arylsulfonylamino-2,2- dichloro-2-phenylethyl)biurets. The reac

Full text of DOI:10.1134/S1070428008100138

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2008, Vol. 44, No. 10, pp. 1486–1489. © Pleiades Publishing, Ltd., 2008.
Original Russian Text © G.N. Rozentsveig, A.V. Popov, I.B. Rozentsveig, G.G. Levkovskaya, 2008, published in Zhurnal Organicheskoi Khimii, 2008,
Vol. 44, No. 10, pp. 1509–1513.
Dedicated to Full Member of the Russian Academy of Sciences
B.A. Trofimov on his 70th anniversary
Reactions of N-(2,2,2-Trichloroethylidene)- and N-(2,2-Dichloro-
2-phenylethylidene)arenesulfonamides with Biuret
G. N. Rozentsveig, A. V. Popov, I. B. Rozentsveig, and G. G. Levkovskaya
Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
e-mail: i_roz@irioch.irk.ru
Received April 30, 2008
Abstract—N-(2,2,2-Trichloroethylidene)- and N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides react
with an equimolar amount of biuret to give 1-(1-arylsulfonylamino-2,2,2-trichloroethyl)- or 1-(1-arylsulfonyl-
amino-2,2-dichloro-2-phenylethyl)biurets. The reactions with 2 equiv of N-(polychloroethylidene)arenesulfon-
amides involve both amino groups in the biuret molecule, yielding the corresponding 1,5-bis(1-arylsulfonyl-
amino-2,2,2-trichloroethyl)- and 1,5-bis(1-arylsulfonylamino-2,2-dichloro-2-phenylethyl)biurets.
DOI: 10.1134/S1070428008100138
Polyamide systems having sulfonamide or urea
fragments attract interest as potential ligands, strong
NH acids [1], catalysts, reagents, and substrates for
asymmetric synthesis and supramolecular chemistry
[2]; they exhibit biological activity [3, 4] and are used
in the synthesis of macrocyclic nitrogen-containing
compounds [5]. Therefore, development of efficient
procedures for the preparation of functionalized poly-
amide systems is an important problem.
Convenient synthetic approaches to various substi-
tuted amide derivatives can be based on transforma-
tions of polyhalogenated aldehyde imines. The pres-
ence of electron-withdrawing groups in molecules of
such Schiff bases considerably activates the CH=N
bond toward nucleophilic reagents, which is widely
used for various synthetic purposes [6].
We previously studied reactions of N-(polychloro-
ethylidene)arenesulfonamides with amides [7, 8], thio-
amides, urea, and phenylurea [9–11] with a view to
develop procedures for selective synthesis of new
functionalized haloalkylamide systems. While continu-
ing studies in this line, in the present work we ex-
amined reactions of N-(2,2,2-trichloroethylidene)- and
N-(2,2-dichloro-2-phenylethylidene)arensulfonamides
Ia–Ic and IIa–IIc with biuret. These reactions were
expected to produce polyamide systems having sulfon-
amide, urea, and polyhaloalkyl fragments, which may
be interesting as potential biologically active sub-
Scheme 1.
O
O
CCl2X O
O
O
H2N
N
NH2
H
ArSO2
ArSO2
N
N
H
N
NH2
H
H
IIIa–IIIc, IVa–IVc
N
CCl2X
O
O
ArSO2
2
CCl2X O
CCl2X
Ia–Ic, IIa–IIc
H2N
N
NH2
H
SO2Ar
N
N
N
N
N
H
H
H
H
H
Va–Vc, VIa–VIc
I, III, V, X = Cl; II, IV, VI, X = Ph; Ar = Ph (a), 4-ClC6H4 (b), 4-MeC6H4 (c).
1486

REACTIONS OF N-(2,2,2-TRICHLOROETHYLIDENE)- ...
1487
stances, ligands, and intermediate products for subse-
quent transformations.
the methine proton. In addition, the spectra contained
broadened singlets due to protons in the (O)CNHC(O)
and NH2 groups and signals from aromatic protons.
The chemical shifts of the NCHN proton in bis-sul-
fonamides Va–Vc and VIa–VIc range from δ 5.0 to
5.5 ppm [12,13]. The downfield shift of the CHCCl2X
Initial Schiff bases Ia–Ic and IIa–IIc were syn-
thesized according to the procedures developed previ-
ously, i.e., by radical reaction of the corresponding
N,N-dichloroarenesulfonamides with trichloroethylene
or phenylacetylene [12, 13]. Biuret reacted with Schiff
bases Ia–Ic and IIa–IIc on heating the reactants to 90–
100°C. The use of dimethylformamide as solvent con-
siderably improves the yield of the addition products
(the reaction mixture is homogeneous). The reactions
of biuret with equimolar amounts of Schiff bases I and
II involved only one amino group in the former, and
the products were the corresponding 1-(1-arylsulfonyl-
amino-2,2,2-trichloroethyl)- and 1-(1-arylsulfonyl-
amino-2,2-dichloro-2-phenylethyl)biurets IIIa–IIIc
and IVa–IVc (Scheme 1). By reactions of biuret with
2 equiv of compounds I and II we obtained 1,5-bis(1-
arylsulfonylamino-2,2,2-trichloroethyl)- and 1,5-bis(1-
arylsulfonylamino-2,2-dichloro-2-phenylethyl)biurets
V and VI, respectively, as a result of condensation in-
volving both NH2 groups in the nucleophilic reagent.
1
proton signal in the H NMR spectra of biuret deriv-
atives III–VI is likely to result from deshielding effect
of the carbonyl group. Compounds III–VI displayed in
the 13C NMR spectra signals corresponding to carbon
atoms in the carbonyl and polyhalomethyl groups,
NCN carbon atom, and carbon atoms in the aromatic
rings.
Substituted biurets III–VI are colorless crystalline
substances which are readily soluble in DMSO, ace-
tone, and aqueous alkali and insoluble in water. The
presence of NHC=O and C–Cl fragments in their
molecules makes them promising as reagents for the
synthesis of nitrogen-containing heterocyclic com-
pounds and complexes with metal salts.
EXPERIMENTAL
Trichloroacetaldehyde derivatives Ia–Ic turned out
to be more reactive in the examined process than the
corresponding dichloro(phenyl)acetaldehyde deriva-
tives IIa–IIc due to stronger electron-withdrawing
effect of the trichloromethyl group as compared to
dichloro(phenyl)methyl. The reaction of biuret with
compounds I required approximately twice as short
time (12 h) as analogous transformation of N-[2,2-di-
chloro-2-phenylethylidene)arenesulfonamides. The
yield of addition products III–VI were 79–97%.
The IR spectra were recorded in KBr on a Bruker
1
IFS-25 spectrometer. The H and 13C NMR spectra
were measured on a Bruker DPX-400 instrument at
400.61 and 100.13 MHz, respectively, using DMSO-d6
as solvent and tetramethylsilane as internal reference.
N-(2,2,2-Trichloroethylidene)arenesulfonamides Ia–Ic
[12] and N-(2,2-dichloro-2-phenylethylidene)arenesul-
fonamides IIa–IIc [13] were prepared according to the
procedures reported previously.
1-(2,2,2-Trichloro-1-phenylsulfonylaminoethyl)-
biuret (IIIa). A mixture of 2.87 g (0.01 mol) of Schiff
base Ia, 1.03 g (0.01 mol) of biuret, and 5 ml of
anhydrous dimethylformamide was stirred for 12 h at
90–100°C. The mixture was poured into 30–40 ml of
water, and the precipitate was filtered off, dried, and
washed with diethyl ether (30–40 ml) until colorless
washings. Yield 3.08 g (79%), mp 220–222°C
(decomp.). IR spectrum, ν, cm–1: 1165, 1330 (SO2);
1690, 1714 (C=O); 3025–3235 br, 3380, 3480 (NH).
The structure of compounds III–VI was proved by
the spectral data and elemental analyses. The IR spec-
tra of new biuret derivatives III–VI contained absorp-
tion bands typical of NH, carbonyl, and sulfonamide
groups. Reduced stretching vibration frequency of the
NH and NH2 groups indicates that they are involved in
hydrogen bonding. Taking into account that molecules
III–VI possess several proton-donor and proton-accep-
tor groups and that internal rotation about the formally
single (O)C–N amide bonds is restricted, both inter-
and intramolecular hydrogen bonds may be formed.
In the 1H NMR spectra of addition products III–VI
in DMSO-d6, protons in the NHCHNH fragment
resonated as a doublet of doublets at δ 5.7–5.9 ppm
(CH) and a doublet and a singlet from the NH protons
in a weaker field (δ 8.6–9.3 ppm). Presumably, the NH
group in the urea fragment is involved in tautomeric
transformations; therefore, the NH signal appears as
a broadened singlet despite spin–spin coupling with
3
1H NMR spectrum, δ, ppm: 5.85 d.d (1H, CH, J =
8.5 Hz); 6.80 br.s (2H, NH2); 7.51 m, 7.63 m, and
7.82 m (5H, C6H5); 8.68 br.s (1H, CONHCO); 8.79 s
3
(1H, CONHCH); 9.24 d (1H, SO2NH, J = 8.5 Hz).
13C NMR spectrum, δC, ppm: 70.44 (CH); 100.99
(CCl3); 126.67, 128.86, 132.75, 140.73 (Carom); 153.19
(CONH2); 155.05 (NHCONH). Found, %: C 30.95;
H 2.67; Cl 27.45; N 14.25; S 8.15. C10H11Cl3N4O4S.
Calculated, %: C 30.83; H 2.85; Cl 27.30; N 14.38;
S 8.23.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 44 No. 10 2008

ROZENTSVEIG et al.
1488
1-[2,2,2-Trichloro-1-(4-chlorophenylsulfonyl-
IIb. Yield 4.25 g (91%), mp 167–169°C. IR spectrum,
ν, cm–1: 1150, 1340 (SO2); 1675, 1700 (C=O); 3250–
3400 br. 1H NMR spectrum, δ, ppm: 5.96 d.d (1H, CH,
3J = 10.3 Hz), 6.83 br.s (2H, NH2), 7.42 m and 7.95 m
(9H, C6H4, C6H5), 8.54 br.s (1H, CONHCO), 8.57 s
amino)ethyl]biuret (IIIb) was synthesized in a similar
way from 3.21 g (0.01 mol) of sulfonamide Ib. Yield
3.73 g (88%), mp 245–247°C (decomp.). IR spectrum,
ν, cm–1: 1150, 1340 (SO2); 1700, 1720 (C=O); 3140,
1
3
3210, 3270, 3340, 3445 (NH). H NMR spectrum, δ,
(1H, CONHCH), 8.86 d (1H, SO2NH, J = 10.3 Hz).
3
ppm: 5.82 d.d (1H, CH, J = 9.5 Hz), 6.64 br.s (2H,
13C NMR spectrum, δC, ppm: 68.23 (CH); 94.60
(CCl2); 126.97, 128.21, 128.61, 128.68, 129.58,
137.32, 138.54, 139.80 (Carom); 152.87 (CONH2),
155.01 (NHCONH). Found, %: C 41.38; H 3.35;
Cl 22.74; N 12.12; S 6.75. C16H15Cl3N4O4S. Calculat-
ed, %: C 41.26; H 3.25; Cl 22.84; N 12.03; S 6.88.
NH2), 7.59 and 7.82 (4H, C6H4, AA′BB′ system),
8.69 br.s (1H, CONHCO), 8.81 s (1H, CONHCH),
3
9.29 d (1H, SO2NH, J = 9.5 Hz). 13C NMR spectrum,
δC, ppm: 70.35 (CH); 100.69 (CCl3); 128.61, 128.86,
137.65, 139.44 (Carom); 153.06 (CONH2); 154.96
(NHCONH). Found, %: C 28.73; H 2.41; Cl 33.86;
N 13.42; S 7.44. C10H10Cl4N4O4S. Calculated, %:
C 28.32; H 2.38; Cl 33.44; N 13.21; S 7.56.
1-[2,2-Dichloro-1-(4-methylphenylsulfonyl-
amino)-2-phenylethyl]biuret (IVc) was synthesized
in a similar way from 3.42 g (0.01 mol) of sulfonamide
IIc. Yield 3.65 g (82%), mp 196–198°C. IR spectrum,
ν, cm–1: 1160, 1325 (SO2); 1660, 1695 (C=O); 3275–
1-[2,2,2-Trichloro-1-(4-methylphenylsulfonyl-
amino)ethyl]biuret (IIIc) was synthesized in a similar
way from 3.01 g (0.01 mol) of sulfonamide Ic. Yield
3.56 g (88%), mp 225–227°C (decomp.). IR spectrum,
ν, cm–1: 1165, 1330 (SO2); 1700, 1720 (C=O); 3100,
1
3440 br (NH). H NMR spectrum, δ, ppm: 2.33 s (3H,
3
CH3), 5.96 d.d (1H, CH, J = 9.8 Hz), 6.67 br.s (2H,
NH2), 7.22 m and 7.66 m (9H, C6H4, C6H5), 8.37 br.s
1
(1H, CONHCO), 8.52 s (1H, CONHCH), 8.65 d (1H,
3135, 3200, 3340, 3455 (NH). H NMR spectrum, δ,
3
SO2NH, J = 9.8 Hz). 13C NMR spectrum, δC, ppm:
ppm: 2.37 s (3H, CH3), 5.81 d.d (1H, CH, 3J = 9.5 Hz),
6.79 br.s (2H, NH2), 7.31 and 7.69 (4H, C6H4, AA′BB′
system), 8.68 br.s (1H, CONHCO), 8.77 s (1H,
21.07 (CH3); 68.27 (CH); 94.88 (CCl2); 126.76,
127.07, 128.25, 129.09, 129.61, 138.20, 138.77, 142.76
(Carom); 152.99 (CONH2); 155.07 (NHCONH). Found,
%: C 45.79; H 3.99; Cl 15.78; N 12.67; S 7.28.
C17H18Cl2N4O4S. Calculated, %: C 45.85; H 4.07;
Cl 15.92; N 12.58; S 7.20.
3
CONHCH), 9.12 d (1H, SO2NH, J = 9.5 Hz).
13C NMR spectrum, δC, ppm: 21.40 (CH3); 70.79
(CH); 101.34 (CCl3); 127.09, 129.61, 138.17, 143.45
(Carom); 153.51 (CONH2); 155.39 (NHCONH). Found,
%: C 32.69; H 3.28; Cl 26.49; N 13.76; S 7.88.
C11H13Cl3N4O4S. Calculated, %: C 32.73; H 3.25;
Cl 26.35; N 13.88; S 7.94.
1,5-Bis(2,2,2-trichloro-1-phenylsulfonylamino-
ethyl)biuret (Va). A mixture of 2.87 g (0.01 mol) of
sulfonamide Ia, 0.52 g (0.005 mol) of biuret, and 5 ml
of DMF was stirred for 12 h at 90–100°C. The mixture
was then treated as described above. Yield 2.85 g
(84%), mp 247–249°C. IR spectrum, ν, cm–1: 1170,
1345 (SO2); 1655, 1690–1715 (C=O); 3250 br (NH).
1-(2,2-Dichloro-2-phenyl-1-phenylsulfonyl-
aminoethyl)biuret (IVa). A mixture of 3.28 g
(0.01 mol) of sulfonamide IIa, 1.03 g (0.01 mol) of
biuret, and 5 ml of DMF was stirred for 20 h at 100°C.
The mixture was then treated as described above. Yield
3.79 g (88%), mp 175–177°C. IR spectrum, ν, cm–1:
1150, 1330 (SO2); 1670, 1700 (C=O); 3275–3455 br
3
1H NMR spectrum, δ, ppm: 5.71 d (2H, CH, J =
9.6 Hz), 7.40 m and 7.94 m (10H, C6H5), 8.89 s
3
(1H, CONHCO), 9.23 d (2H, SO2NH, J = 9.6 Hz).
13C NMR spectrum, δC, ppm: 70.40 (CH); 100.69
(CCl3); 126.68, 128.88, 132.91, 140.39 (Carom); 162.50
(C=O). Found, %: C 32.48; H 2.56; Cl 31.68; N 10.78;
S 9.68. C18H17Cl6N5O6S2. Calculated, %: C 31.97;
H 2.53; Cl 31.46; N 10.36; S 9.48.
1
(NH). H NMR spectrum, δ, ppm: 5.95 d.d (1H, CH,
3J = 10.0 Hz), 6.80 br.s (2H, NH2), 7.52 m and 7.82 m
(10H, C6H5), 8.53 br.s (1H, CONHCO), 8.59 s (1H,
3
CONHCH), 8.84 d (1H, SO2NH, J = 10.0 Hz).
13C NMR spectrum, δC, ppm: 67.33 (CH); 94.98
(CCl2); 126.67, 128.15, 128.56, 128.86, 129.49,
136.98, 138.42, 139.73 (Carom); 152.68 (CONH2);
154.28 (NHCONH). Found, %: C 44.73; H 3.71;
Cl 16.52; N 12.85; S 7.35. C16H16Cl2N4O4S. Calcula-
ted, %: C 44.56; H 3.74; Cl 16.44; N 12.99; S 7.43.
1,5-Bis[2,2,2-trichloro-1-(4-chlorophenylsul-
fonylamino)ethyl]biuret (Vb) was synthesized in
a similar way from 3.21 g (0.01 mol) of sulfonamide
Ib. Yield 3.82 g (90%), mp 252–254°C (decomp.). IR
spectrum, ν, cm–1: 1170, 1345 (SO2); 1670 br (C=O);
1
3275–3380 br (NH). H NMR spectrum, δ, ppm:
1-[2,2-Dichloro-1-(4-chlorophenylsulfonyl-
amino)-2-phenylethyl]biuret (IVb) was synthesized
in a similar way from 3.64 g (0.01 mol) of sulfonamide
5.72 d (2H, CH, 3J = 8.0 Hz), 7.51 and 7.75 (8H, C6H4,
AA′BB′ system), 8.99 s (1H, CONHCO), 9.34 d (2H,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 44 No. 10 2008

REACTIONS OF N-(2,2,2-TRICHLOROETHYLIDENE)- ...
1489
3
SO2NH, J = 8.0 Hz). 13C NMR spectrum, δC, ppm:
1,5-Bis[2,2-dichloro-1-(4-methylphenylsulfonyl-
amino)-2-phenylethyl]biuret (VIc) was synthesized
in a similar way from 3.42 g (0.01 mol) of sulfonamide
IIc. Yield 3.51 g (89%), mp 82–84°C. IR spectrum, ν,
cm–1: 1165, 1340 (SO2); 1660 (C=O); 3275–3370 br
71.57 (CH); 101.68 (CCl3); 129.85, 130.13, 139.00,
140.50 (Carom); 153.71 (C=O). Found, %: C 29.22;
H 2.09; Cl 38.45; N 9.25; S 8.45. C18H15Cl8N5O6S2.
Calculated, %: C 29.02; H 2.03; Cl 38.07; N 9.40;
S 8.61.
1
(NH). H NMR spectrum, δ, ppm: 2.34 s (6H, CH3);
3
5.93 d.d (2H, CH, J = 9.4, 10.1 Hz), 7.32 m and
1,5-Bis[2,2,2-trichloro-1-(4-methylphenylsul-
fonylamino)ethyl]biuret (Vc) was synthesized in
a similar way from 3.01 g (0.01 mol) of sulfonamide
Ic. Yield 3.65 g (86%), mp 236–238°C. IR spectrum,
ν, cm–1: 1170, 1340 (SO2); 1680 br (C=O); 3250–
7.98 m (18H, C6H4, C6H5), 8.49 s (1H, CONHCO),
3
8.82 d (2H, CONHCH, J = 9.4 Hz), 8.87 d (2H,
3
SO2NH, J = 10.1 Hz). 13C NMR spectrum, δC, ppm:
24.73 (CH3); 68.85 (CH); 94.58 (CCl2); 124.99,
127.03, 127.45, 127.99, 128.08, 128.67, 129.12, 129.62
(Carom); 152.96 (C=O). Found, %: C 48.85; H 3.95;
Cl 18.11; N 8.95; S 8.05. C32H31Cl4N5O6S2. Calculat-
ed, %: C 48.80; H 3.97; Cl 18.01; N 8.89; S 8.14.
1
3320 br (NH). H NMR spectrum, δ, ppm: 2.28 s (6H,
CH3), 5.74 d (2H, CH, 3J = 9.9 Hz), 7.23 and 7.62 (8H,
C6H4, AA′BB′ system), 8.88 s (1H, CONHCO), 9.05 d
(2H, SO2NH, J = 9.9 Hz). 13C NMR spectrum, δC,
3
ppm: 20.49 (CH3); 71.04 (CH); 100.98 (CCl3); 127.55,
128.92, 137.68, 140.25 (Carom); 153.53 (C=O). Found,
%: C 34.38; H 3.09; Cl 30.28; N 9.86; S 9.25.
C20H21Cl6N5O6S2. Calculated, %: C 34.11; H 3.01;
Cl 30.20; N 9.94; S 9.10.
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1,5-Bis(2,2-dichloro-2-phenyl-1-phenylsulfonyl-
aminoethyl)biuret (VIa). A mixture of 3.28 g
(0.01 mol) of sulfonamide IIa, 0.52 g (0.005 mol) of
biuret, and 5 ml of DMF was stirred for 20 h at 100°C.
The mixture was then treated as described above. Yield
3.50 g (92%), mp 85–87°C. IR spectrum, ν, cm–1:
1160, 1340 (SO2); 1655, 1700 (C=O); 3275–3360 br
vol. 119, p. 6452.
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6. Levkovskaya, G.G., Drozdova, T.I., Rozentsveig, I.B.,
1
(NH). H NMR spectrum, δ, ppm: 5.94 d.d (2H, CH,
3J = 9.6, 10.2 Hz), 7.35 m and 7.95 m (20H, C63H5),
8.58 s (1H, CONHCO), 8.83 d (2H, CONHCH, J =
and Mirskova, A.N., Usp. Khim., 1999, vol. 68, p. 638.
3
9.6 Hz), 8.85 d (2H, SO2NH, J = 10.2 Hz). 13C NMR
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127.22, 127.89, 128.13, 128.20, 128.86, 128.99, 129.85
(Carom); 152.79 (C=O). Found, %: C 47.56; H 3.48;
Cl 18.55; N 9.25; S 8.25. C30H27Cl4N5O6S2. Calculat-
ed, %: C 47.44; H 3.58; Cl 18.67; N 9.22; S 8.44.
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1,5-Bis[2,2-dichloro-1-(4-chlorophenylsulfonyl-
amino)-2-phenylethyl]biuret (VIb) was synthesized
in a similar way from 3.64 g (0.01mol) of sulfonamide
IIb. Yield 4.04 g (97%), mp 78–80°C. IR spectrum, ν,
cm–1: 1170, 1340 (SO2); 1660, 1700 (C=O); 3280–
1
3370 br (NH). H NMR spectrum, δ, ppm: 5.95 d.d
3
(2H, CH, J = 9.5, 10.0 Hz), 7.39 m and 7.95 m (18H,
C6H4, C6H5), 8.58 s (1H, CONHCO), 8.83 d (2H,
3
3
CONHCH, J = 9.5 Hz), 8.86 d (2H, SO2NH, J =
10.0 Hz). 13C NMR spectrum, δC, ppm: 69.26 (CH);
94.60 (CCl2); 126.94, 127.33, 127.55, 127.97, 128.00,
128.76, 129.00, 129.58 (Carom); 152.84 (C=O). Found,
%: C 43.65; H 3.09; Cl 25.46; N 8.39; S 7.78.
C30H25Cl6N5O6S2. Calculated, %: C 43.50; H 3.04;
Cl 25.68; N 8.45; S 7.74.
13. Drozdova, T.I., Levkovskaya, G.G., and Mirskova, A.N.,
Zh. Org. Khim., 1992, vol. 28, p. 1236.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 44 No. 10 2008