Reaction of N-arylsulfonyl-2(3)-arylsulfonylamino-substituted 1,4-benzoquinonimines with sodium arylsulfinates

Article abstract of DOI:10.1134/S1070428014020109

N-Arylsulfonyl-3-arylsulfonylamino-substituted 1,4-benzoquinonimine reacts with sodium arylsulfinates regiospecifically along 1,4-addition scheme; N-tosyl-2-(tosylamino)-substituted 1,4-benzoquinonimine regioselectively affords products of 1,4- and 6,3-ad

Full text of DOI:10.1134/S1070428014020109

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2014, Vol. 50, No. 2, pp. 200−204. © Pleiades Publishing, Ltd., 2014.
Original English Text © S.A. Konovalova, A.P. Avdeenko, A.A. Santalova, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 2, pp. 209−213.
Reaction of N-Arylsulfonyl-2(3)-arylsulfonylamino-Substituted
1,4-Benzoquinonimines with Sodium Arylsulfinates
S. A. Konovalova, A. P. Avdeenko, and A. A. Santalova
Donbass State Engineering Academy, Kramatorsk, 84313 Ukraine
е-mail: chimist@dgma.donetsk.ua
Received October 25, 2013
Abstract—N-Arylsulfonyl-3-arylsulfonylamino-substituted 1,4-benzoquinonimine reacts with sodium
arylsulfinates regiospecifically along 1,4-addition scheme; N-tosyl-2-(tosylamino)-substituted 1,4-benzoquinonimine
regioselectively affords products of 1,4- and 6,3-addition with the latter prevailing. Arylsulfinate anion enters
predominantly in the para-position with respect to the ArSO2NH group.
DOI: 10.1134/S1070428014020109
This study is a continuation of the research on the
reactions of N-substituted 1,4-benzoquinonimines with
nucleophilic reagents. It was formerly established that
N-arylsulfonyl-2(3)-arylsulfonylamino-substituted
1,4-benzoquinonimines reacted regiospecifically with
hydrazoic acid and aromatic amines. Nucleophiles N3–
andArNH– enter exclusively in the para-position with
respect to the ArSO2NH group forming the products
of 6,3- and 1,4-addition respectively [1–3]. The
addition of hydrogen chloride to N-aryl-sulfonyl-2(3)-
arylsulfonylamino-substituted 1,4-benzoquinonimine
also proceeds regiospecifically, but in both cases the
chlorine atom of the HCl molecule adds only in the
position 6 of the quinoid ring giving a single isomer, the
product of 1,4-addition [2, 4]. These differences may
be ascribed to different hardness of the nucleophiles.
precipitate isolated from the reaction mixture, the product
obtained by crystallization, and the precipitate obtained
from the filtrate after crystallization.
As showed the experiments, N-arylsulfonyl-3-
arylsulfonylamino-substituted 1,4-benzoquinonimines
Ia, Ib added the arylsulfinate ion exclusively to the
para-position with respect to the ArSO2NH group with
the formation of products of 1,4-addition IVa, IVb (see
the scheme), similarly to the reaction with sodium azide
[1], aromatic amines [2, 3], and hydrogen chloride [2, 4].
The 1Н NMR spectra of compounds IVa, IVb contain two
singlets of protons Н3 and Н6 in the regions δ 7.04−7.10
and 6.87−6.88 ppm.
N-(Tosyl)-2-(tosylamino)-substituted 1,4-benzo-
quinonimine (II) reacting with sodium arylsulfinates
IIIа, IIIb gives simultaneously two reaction products by
1,4-addition (Vа, Vb) and by 6,3-addition (VIа, VIb) into
the para-position with respect to TsNH group with the
prevalence of the latter compound. The reaction mixture
contained also an insignificant quantity of compound
VII, the reduced form of the initial quinonimine (see the
The target of this study was investigation of
the reaction between N-arylsulfonyl-2(3)-aryl-
sulfonylamino-substitute 1,4-benzoquinonimines Ia,
Ib, II and soft nucleophiles, sodium arylsulfinates.
The reaction of benzoquinonimines Ia, Ib, II
with sodium arylsulfinates IIIa, IIIb was carried
out in acetic acid at the reagents ratio 1 : 2. Mе and
MеО groups were mainly utilized as substituents in
the para-position of the arylsulfonyl fragments of
quinonimines and sodium arylsulfinates in order to
simplify the assignment of the proton signals in the
1Н NMR spectra.
1
scheme). According to Н NMR data the percent ratio
in the reaction mixture of isomers Vа, VIа was 42 : 58,
and isomers Vb, VIb, 41 : 59. By several consecutive
crystallizations we succeeded to isolate compounds Vа,
VIа, VIb in an individual state.
The structure of compounds VIа, VIb is confirmed
by 1Н NMR spectra where the signals of protons Н2 and
Н5 from the phenol fragment appear as singlets at δ 7.22
and 7.40 (VIа) and at δ 7.22 and 7.39 ppm (VIb). In
To discover all probable reaction products we
analyzed by 1Н NMR spectroscopy the noncrystallized
200

REACTION OF N-ARYLSULFONYL-2(3)-ARYLSULFONYLAMINO-SUBSTITUTED
201
Scheme.
IVa, IVb, Va, Vb
R3
Ia, Ib, II
VIa, VIb
IIIa, IIIb
I, R1 = R3 = H, R2 = NHSO2C6H5 (a); R1 = H, R2 = TsNH, R3 = Mе (b); II, R1 = TsNH, R2 = H, R3 = Mе; III, R4 = Me (a),
MеO (b); IV, R1 = R3 = H, R2 = NHSO2C6H5, R4 = MeO (a); R1 = H, R2 = TsNH, R3 = Mе, R4 = MeO (b); V, R1 = TsNH,
R2 = H; R3 = R4 = Me (a); R3 = Me, R4 = MеO (b); VI, R1 = Me (a), MеO (b); VIII, R1 = R3 = H, R2 = NHSO2C6H5, R4 =
MeO (a); R1 = H, R2 = TsNH, R3 = Mе, R4 = MeO (b); IX, R1 = TsNH, R2 = H, R3 = R4 = Mе.
the 1Н NMR spectra of products of 1,4-addition Vа, Vb
the protons Н3 and Н5 of the phenol fragment appear as
doublets due to the spin-spin coupling with meta-protons
at δ 7.39, 7.19 (Vа) and 7.37, 7.20 ppm (Vb) respectively.
IVb, Va were oxidized with lead tetraacetate in glacial
acetic acid into the corresponding quinonimines VIIIа,
VIIIb, IX, for the 1НNMR spectra of quinonemonoimines
1
were more informative. In the Н NMR spectrum of
quinonimine IX the doublets of protons Н3 and Н5 of
the quinoid fragment appear with the coupling constant
8.1 Hz at 7.96 and 7.78 (Z-isomer) and with the coupling
constant 2.4 Hz at 9.05 and 6.79 ppm (Е-isomer). In
It should be mentioned that the structure determination
of the products of addition to quinonimine II provided
certain difficulties, since in the precipitates obtained
from the reaction mixture always three compounds were
present (considering the presence of the reduced form of
the initial quinonimine), therefore the 1Н NMR spectra in
the region 6.00–8.00 ppm were very intricate. When we
failed to isolate individual compounds from the mixture
the ratio of the reaction products was estimated from the
integral intensity of the protons from the MеО and Mе
groups since the signals of the MеО protons belonging
to the added arylsulfinate ion possessed characteristic
chemical shifts for the products of 1,4- (δ 3.81−3.82 ppm)
and 6,3- (δ 3.84 ppm) addition.
1
the Н NMR spectra of quinonimines VIIIа, VIIIb
the singlets of protons Н3 and Н6 of the quinoid ring
are observed at 8.88, 6.41 (VIIIа) and 8.88, 6.37 ppm
(VIIIb) unambiguously proving the assumed structure of
compounds VIIIа, VIIIb, IX as products of 1,4-addition.
Thus the performed research resulted in establishing
that N-arylsulfonyl-3-(arylsulfonylamino)-substituted
1,4-benzoquinonimines reacted with sodium arylsulfinates
regiospecifically along the 1,4-addition scheme,
whereas N-(4-tosyl)-2-(4-tosyl)amino-substituted
1,4-benzoquinonimine reacted regioselectively adding the
arylsulfinate ion in 1,4- and 6,3-positions with the latter
In order to confirm once more the structure of the
obtained compounds the products of 1,4-addition IVa,
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KONOVALOVA et al.
202
direction prevailing. Basing on the above it is possible
to conclude that the main factor governing the site of
the attack of arylsulfinate ion on the quinonimine is the
position ofArSO2NH group in the quinoid fragment: The
arylsulfinate ion adds exclusively to the para-position
with respect toArSO2NH group in 3-(arylsulfonylamino)-
substituted 1,4-benzoquinonimines and predominantly
to the para-position with respect to ArSO2NH group in
2-(arylsulfonylamino) derivatives.
Hence the performed experiments made it possible
to establish that in reactions of N-arylsulfonyl-2(3)-
(arylsulfonylamino)-substituted 1,4-benzoquinonimines
with sodium arylsulfinates the orientation of the addition
of arylsulfinate ion in the quinonimine ring is mainly
governed by ArSO2NH group.
EXPERIMENTAL
1Н NMR spectra were registered on a spectrometer
Varian VXR-300 (300 MHz), internal reference TMS. The
purity of quinonimines VIIIа, VIIIb, IX was checked
by TLC on Silufol UV-254 plates, solvent chloroform,
eluent benzene–hexane, 10 : 1, and development under
UV irradiation.
The N-arylsulfonyl-2(3)-(arylsulfonylamino)-sub-
stituted 1,4-benzoquinonimines are characterized by
ortho-para-quinoid tautomerism [2, 5]. In the nucleophilic
addition reactions in most cases the N-arylsulfonyl-1,4-
benzoquinonemonoimines direct the nucleophile (in
particular, the sulfinate ion) in positions 2 and 6 of the
quinoid ring [6–8], and о-quinonimines, in positions 1
and 6 [5]. In the N-arylsulfonyl-3-(arylsulfonylamino)
derivatives of 1,4-benzoquinonimine I both ortho- and
para-quinoid forms have concerted orientation. In
quinonimines I in their p-quinoid form A the position 2 is
shielded withArSO2NH group, and in the o-quinoid form
B the position 1 is occupied by the ОН group. Therefore
the arylsulfinate ion attacks only the position 6, and the
regiospecific 1,4-addition is observed.
Quinonimine II was synthesized by procedure [9] by
the oxidation of 2,4-bis(p-toluenesulfonylamino)phenol
with lead tetraacetate in acetic acid. Quinonimines Ia,
Ib were prepared by method [2] by the oxidation of the
appropriate o-phenylenedi(arylsulfonylamides) with io-
dozobenzene diacetate in the presence of boron trifluoride
etherate in acetic acid medium. Sodium arylsulfinates
IIIа, IIIb were prepared as described in [10].
Characteristics of quinonimines Ia, Ib [2], II [9] are
in agreement with published data.
ArSO2NH
ArSO2N
3
2
3
2
Reactions of quinonimines Iа, Ib, II with sodium
arylsulfinates IIIа, IIIb. To a boiling solution of
2 mmol of quinonimine in 20 mL of glacial acetic acid
was added in one portion 4 mmol of an appropriate
sodium arylsulfinate IIIa, IIIb, and the mixture was
stirred. After discoloration of the solution within several
minutes the solution was cooled, and water was added
till complete precipitation of reaction products. The
colorless precipitate was filtered off and washed with
water. A part of the precipitate was recrystallized from
acetic acid. The filtrate obtained at the recrystallization
was diluted with water, the separated precipitate was
filtered off. The obtained precipitates were studied by
1Н NMR spectroscopy.
1
4
4
1
ArSO2N
O
ArSO2N
OH
5
5
6
6
*
*
A
B
I
In N-arylsulfonyl-2-(arylsulfonylamino) derivative
II the orientation of para- and ortho-quinoid forms
is not concerted. In the para-quinoid form C of
quinonemonoimines II the active position is the position
6 of quinoid ring, and in the ortho-quinoid form D, the
position 5 of quinoid ring (position 4 is occupied with
ArSO2NH group).As mentioned above, for compound II
both 1,4- and 6,3-additions occur with the prevalence of
the latter due to the stronger orienting effect ofArSO2NH
group into the para-position 5, regardless of the presence
of a bulky group in the position 4.
2-(4-Methoxyphenylsulfonyl)-4,5-bis(phenyl-
sulfonylamino)phenol (IVа). Yield 83%, mp 177−178°C.
NHSO2Ar
NSO2Ar
3
2
3
2
1
1
4
4
ArSO2N
O
ArSO2NH
O
6
5
5
6
C
*
*
D
II
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REACTION OF N-ARYLSULFONYL-2(3)-ARYLSULFONYLAMINO-SUBSTITUTED
203
1Н NMR spectrum (DMSO-d6), δ, ppm: 3.82 s (3Н,
MеО), 6.88 s (1Н, Н6), 7.04 s (1Н, Н3), 7.07 d (2Н,
4-MеОС6Н4, Н6,2, J 9.0 Hz), 7.50 d (2Н, 4-MеОС6Н4,
Н5,3, J 9.0 Hz), 7.57−7.88 m (10Н, 2Ph), 9.42 s (1Н,
NH), 9.58 br.s (1Н, NH), 10.96 s (1Н, ОН). Found, %:
N 4.81, 5.06; S 17.04, 16.65. C25H22N2O8S3. Calculated,
%: N 4.87; S 16.74.
7.34 d (2Н, 4-MеС6Н4SO2NH, Н6′,2′, J 8.4 Hz), 7.36 d
(2Н, 4-MеС6Н4SO2, Н6′′,2′′, J 7.8 Hz), 7.40 s (1Н, Н5),
7.53 d (2Н, 4-MеС6Н4SO2NH, Н5,3, J 8.1 Hz), 7.56 d
(2Н, 4-MеС6Н4SO2, Н5′′,3′′, J 7.8 Hz), 7.63 d (2Н,
4-MеС6Н4SO2NH, Н5′,3′, J 8.4 Hz), 9.09 s (1Н, NH),
9.91 br.s (1Н, NH), 10.56 br.s (1Н, ОН). Found, %:
N 4.60, 4.86; S 16.73, 16.55. C27H26N2O7S3. Calculated,
%: N 4.77; S 16.40.
2-(4-Methoxyphenylsulfonyl)-4,5-bis(tosyl-
amino)phenol (IVb). Yield 87%, mp 240−241°C.
1Н NMR spectrum (DMSO-d6), δ, ppm: 2.35 s (3Н,
4-MеС6Н4SO2NH), 2.42 s (3Н, 4-MеС6Н4SO2NH), 3.82 s
(3Н, MеО), 6.87 s (1Н, Н6), 7.07 d (2Н, 4-MеОС6Н4, Н6,2,
J 8.7 Hz), 7.08 s (1Н, Н3), 7.38 d (2Н, 4-MеС6Н4SO2NH,
3-(4-Methoxyphenylsulfonyl)-4,6-bis(tosylamino)
phenol (VIb). Yield 28%, mp 185–187°C.
1Н NMR spectrum (DMSO-d6), δ, ppm: 2.35 s (6Н,
2×4-MеС6Н4SO2NH), 3.84 s (3Н, MеО), 7.06 d (2Н,
4-MеОС6Н4, Н6,2, J 8.1 Hz), 7.22 s (1Н, Н2), 7.30 d
(2Н, 4-MеС6Н4SO2NH, Н6′,2′, J 7.5 Hz), 7.34 d (2Н,
4-MеС6Н4SO2NH, Н6′′,2′′, J 7.5 Hz), 7.39 s (1Н, Н5),
7.54 d (2Н, 4-MеС6Н4SO2NH, Н5′,3′, J 7.5 Hz), 7.62 d
(2Н, 4-MеС6Н4SO2NH, Н5′′,3′′, J 7.5 Hz), 7.63 d (2Н,
4-MеОС6Н4, Н5,3, J 8.1 Hz), 9.13 br.s (1Н, ОН),
10.23 br.s (2Н, NH). Found, %: N 4.41, 4.59; S 16.26,
16.38. C27H26N2O8S3. Calculated, %: N 4.65; S 15.96.
2,4-Bis(tosylamino)phenol (VII). 1Н NMR spectrum
(DMSO-d6), δ, ppm: 2.32 s (3Н, 4-MеС6Н4SO2), 2.34 s
(3Н, 4-MеС6Н4SO2NH), 6.51 d (1Н, Н6, J 8.7 Hz),
6.57 d.d (1Н, Н5, J 8.4 Hz), 7.12 d (1Н, Н3, J 2.4 Hz),
7.27 d (2Н, 4-MеС6Н4SO2NH, Н6,2, J 7.8 Hz), 7.30 d
(2Н, 4-MеС6Н4SO2NH, Н5,3, J 7.8 Hz), 7.51 d (2Н,
4-MеС6Н4SO2NH, Н6′,2′, J 8.4 Hz), 7.53 d (2Н,
4-MеС6Н4SO2NH, Н5′,3′, J 8.4 Hz), 9.34 br.s (1Н, NH),
9.48 br.s (1Н, NН), 9.70 br.s (1Н, ОН).
Н6′,2′, J 7.8 Hz), 7.41 d (2Н, 4-MеС6Н4SO2NH, Н6′′,2′′
,
J 7.8 Hz), 7.53 d (2Н, 4-MеС6Н4SO2NH, Н5′,3′, J 7.8 Hz),
7.53 d (2Н, 4-MеС6Н4SO2NH, Н5′′,3′′, J 7.8 Hz), 7.75 d
(2Н, 4-MеОС6Н4, Н5,3, J 8.7 Hz), 9.36 s (1Н, NH),
9.43 br.s (1Н, NН), 10.94 s (1Н, ОH). Found, %: N 4.74,
4.47; S 15.58, 15.96. C27H26N2O8S3. Calculated, %:
N 4.65; S 15.96.
2-Tosyl-4,6-bis(tosylamino)phenol (Vа). Yield
1
26%, mp 207−208°C. Н NMR spectrum (DMSO-d6),
δ, ppm: 2.36 s (6Н, 2×4-MеС6Н4SO2NH), 2.39 s
(3Н, 4-MеС6Н4SO2), 7.19 d (1Н, Н5, J 2.7 Hz),
7.27 d (2Н, 4-MеС6Н4SO2NH, Н6,2, J 8.1 Hz), 7.34 d
(2Н, 4-MеС6Н4SO2, Н6′,2′, J 7.8 Hz), 7.37 d (2Н,
4-MеС6Н4SO2, Н6′′,2′′, J 8.4 Hz), 7.39 d (1Н, Н3,
J 2.7 Hz), 7.48 d (2Н, 4-MеС6Н4SO2NH, Н5,3, J 8.1 Hz),
7.49 d (2Н, 4-MеС6Н4SO2, Н5′′,3′′, J 8.4 Hz), 7.55 d (2Н,
4-MеС6Н4SO2, Н5′,3′, J 7.8 Hz), 9.33 br.s (1Н, NH),
9.68 br.s (1Н, NH), 10.16 br.s (1Н, ОН). Found, %:
N 7.14, 6.88; S 15.69, 15.99. C18H14N2O5S2. Calculated,
%: N 6.96; S 15.93.
4-Imino-2-(4-methoxyphenylsulfonyl)-5-(phenyl-
sulfonylamino)-N-(phenylsulfonyl)-cyclohexa-2,5-
dien-1-one (VIIIа). Yield 73%, mp 163–165°C. 1Н NMR
spectrum (CDCl3), δ, ppm: 3.88 s (3Н, MеО), 6.41 s
(1Н, Н6), 7.00 d (2Н, 4-MеОС6Н4, Н6,2, J 8.7 Hz),
7.51−8.04 m (10Н, 2Ph), 7.65 s (1Н, NH), 7.99 d (2Н,
4-MеОС6Н4, Н5,3, J 8.7 Hz), 8.88 s (1Н, Н3). Found, %:
N 5.05, 5.16; S 16.63, 17.11. C25H20N2O8S3. Calculated,
%: N 4.89; S 16.80.
2-(4-Methoxyphenylsulfonyl)-4,6-bis(tosylamino)-
1
phenol (Vb). Н NMR spectrum (DMSO-d6), δ, ppm:
2.35 s (6Н, 2×4-MеС6Н4SO2), 3.81 s (3Н, MеО), 7.08 d
(2Н, 4-MеОС6Н4, Н6,2, J 8.7 Hz), 7.20 d (1Н, Н5,
J 2.7 Hz), 7.27 d (2Н, 4-MеС6Н4SO2NH, Н6′,2′, J 8.1 Hz),
7.37 d (1Н, Н3, J 3.0 Hz), 7.39 d (2Н, 4-MеС6Н4SO2NH,
Н6′′,2′′, J 8.4 Hz), 7.47 d (2Н, 4-MеС6Н4SO2NH, Н5′,3′
,
4-Imino-2-(4-methoxyphenylsulfonyl)-N-tosyl-5-
(tosylamino)cyclohexa-2,5-dien-1-one (VIIIb). Yield
J 8.1 Hz), 7.50 d (2Н, 4-MеС6Н4SO2NH, Н5′′,3′′, J 8.4 Hz),
7.76 d (2Н, 4-MеОС6Н4, Н5,3, J 8.7 Hz), 9.06 s (1Н, NH),
9.75 s (1Н, NH), 10.16 s (1Н, ОН).
1
82%, mp 185–187°C. Н NMR spectrum (CDCl3),
δ, ppm: 2.43 (3Н, 4-MеС6Н4SO2NH), 2.53 s (3Н,
4-MеС6Н4SO2N), 3.88 s (3Н, MеО), 6.37 s (1Н,
Н6), 7.00 d (2Н, 4-MеОС6Н4, Н6,2, J 9.0 Hz), 7.32 d
(2Н, 4-MеС6Н4SO2NH, Н6′,2′, J 8.1 Hz), 7.46 d (2Н,
4-MеС6Н4SO2N, Н6′′,2′′, J 8.1 Hz), 7.69 s (1Н, NH),
7.90 d (2Н, 4-MеС6Н4SO2NH, Н5′,3′, J 8.1 Hz), 7.90 d
3-Tosyl-4,6-bis(tosylamino)phenol (VIа). Yield
1
30%, mp 224−226°C. Н NMR spectrum (DMSO-d6),
δ, ppm: 2.35 s (3Н, 4-MеС6Н4SO2NH), 2.37 s (3Н,
4-MеС6Н4SO2NH), 2.38 s (3Н, 4-MеС6Н4SO2), 7.22 s
(1Н, Н2), 7.29 d (2Н, 4-MеС6Н4SO2NH, Н6,2, J 8.1 Hz),
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KONOVALOVA et al.
204
(2Н, 4-MеС6Н4SO2N, Н5′′,3′′, J 8.1 Hz), 7.99 d (2Н,
4-MеОС6Н4, Н5,3, J 9.0 Hz), 8.88 s (1Н, Н3). Found, %:
N 4.39, 4.62; S 16.30, 16.56. C27H24N2O8S3. Calculated,
%: N 4.66; S 16.01.
S 16.60, 16.71. C27H24N2O7S3. Calculated, %: N 4.79;
S 16.45.
REFERENCES
4-Imino-2-tosyl-6-(tosylamino)-N-(tosyl)-cyclo-
hexa-2,5-dien-1-one (IX). Yield 76%, mp 209–210°C.
1Н NMR spectrum (CDCl3), δ, ppm, Е-isomer: 2.44 s
(3Н, 4-MеС6Н4SO2NH), 2.45 s (3Н, 4-MеС6Н4SO2N),
2.48 s (3Н, 4-MеС6Н4SO2), 6.79 d (1Н, Н5, J 2.4 Hz),
7.34 d (2Н, 4-MеС6Н4SO2NH, Н6,2, J 8.1 Hz), 7.40 d
(2Н, 4-MеС6Н4SO2, Н6′,2′, J 8.1 Hz), 7.40 d (2Н,
4-MеС6Н4SO2N, Н6′′,2′′, J 8.1 Hz), 7.75 br.s (1Н, NH),
7.86 d (2Н, 4-MеС6Н4SO2, Н5′,3′, J 8.1 Hz), 7.91 d
(2Н, 4-MеС6Н4SO2NH, Н5,3, J 8.1 Hz), 7.92 d (2Н,
4-MеС6Н4SO2N, Н5′′,3′′, J 8.1 Hz), 9.05 d (1Н, Н3,
J 2.4 Hz); Z-isomer: 2.44 s (3Н, 4-MеС6Н4SO2NH),
2.45 s (3Н, 4-MеС6Н4SO2N), 2.48 s (3Н, 4-MеС6Н4SO2),
7.34 d (2Н, 4-MеС6Н4SO2NH, Н6,2, J 8.1 Hz), 7.40 d
(2Н, 4-MеС6Н4SO2, Н6′,2′, J 8.1 Hz), 7.40 d (2Н,
4-MеС6Н4SO2N, Н6′′,2′′, J 8.1 Hz), 7.72 br.s (1Н, NH),
7.78 d (1Н, Н5, J 2.4 Hz), 7.86 d (2Н, 4-MеС6Н4SO2,
Н5′,3′, J 8.1 Hz), 7.91 d (2Н, 4-MеС6Н4SO2NH, Н5,3,
J 8.1 Hz), 7.92 d (2Н, 4-MеС6Н4SO2N, Н5′′,3′′, J 8.1 Hz),
7.96 d (1Н, Н3, J 2.4 Hz). Found, %: N 4.75, 4.97;
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