Full Papers
doi.org/10.1002/cplu.202000326
ChemPlusChem
1
1634; 1595; 1504. HRMS calcld. [C12H11FN2O2S+H]+ 267.0598; found
m/z 267.0599 [M+H]+.
powder, in 26% yield. H NMR (400 MHz, DMSO-d6) δ: 10.06 (s, 1H,
1
2
3
4
5
6
7
8
9
NH), 9.07 (s, 1H, NH), 8.87 (s,1H, NH), 7.58(m, 4H, ArH), 7.43 (d, 2H,
ArH, J=7.9 Hz), 7.27 (t, 2H, ArH, J=7.8 Hz), 7.07 (m, 4H), 6.98 (t, 2H,
ArH, J=7.4 Hz) ppm. 13C NMR (100 MHz, DMSO-d6) δ: 159.4 (d, J=
241.0 Hz); 152.6; 144.3; 139.6; 134.6 (d, J=2.6 Hz); 131.7; 129.3;
128.5; 123.1 (d, J=8.2 Hz); 122.7; 118.9; 118.0; 116.3 (d, J=22.6 Hz)
ppm. 19F NMR (100 MHz, DMSO-d6) δ: À 118.7 ppm. IR vmax/cmÀ 1
3377; 3359; 3146; 2951; 1733; 1689; 1590; 1543; 1504. HRMS calcld.
[C19H16FN3O3S+H]+ 386.0969; found m/z 386.0960 [M+H]+. Mp.:
Ethyl-4-((4-aminophenyl)sulphonamido)benzoate 3d: Starting
from ethyl-4-((4-nitrophenyl)sulphonamido)benzoate 2d, the prod-
uct 3d was synthesized according to general procedure. The title
1
compound was obtained as orange powder, in 94% yield. H NMR
(400 MHz, DMSO-d6) δ: 10.43 (s, 1H, NH), 7.79 (d, 2H, ArH, J=8.8 Hz),
7.44 (d, 2H, ArH, J=8.8 Hz), 7.17 (d, 2H, ArH, J=8.8 Hz), 6.54 (d, 2H,
ArH, J=8.8 Hz), 6.03 (s, 2H, NH2), 4.24 (q, 2H, O-CH2 -, J=7.1 Hz),
1.27 (s, 3H, CH3, J=7.1 Hz) ppm. 13C NMR (100 MHz, DMSO-d6) δ:
165.6; 153.6; 143.5; 130.9; 129.3; 124.3; 124.2; 117.9; 113.0; 60.8;
14.6 ppm. IR vmax/cmÀ 1 3453; 3375; 3201; 3056; 2941; 1687; 1642;
1597; 1507. HRMS calcld. [C15H16N2O4S+H]+ 321.0903; found m/z
321.0903 [M+H]+.
°
105.6–107.8 C. X-ray data: monoclinic system, space group P21/n,
a=9.1509(4), b=7.1990(3), c=30.7219(14) Å, β=91.632(2) , Z=4,
°
V=2023.06(2) Å3, Dc=1.40 g.cm-3, μ(Mo Kα)=0,201 mm-1, T=
120 K, crystal dimensions of 0.04×0.17×0.23 mm, colourless prism.
It was necessary to model a disorder of ethyl acetate solvate
molecule. The heavy atoms with a partial occupancy were refined
only isotropically. The structure converged to the final R=0.0679
and Rw=0.1773 using 3885 independent reflections for 329 refined
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
N-((4-trifluoromethyl)phenyl)-4-aminobenzene sulphonamide 3e:
Starting from N-((4-trifluoromethyl)phenyl)-4-nitrobenzene sulpho-
namide 2e, the product 3e was synthesized according to general
procedure. The title compound was obtained as white powder, in
°
parameters (θmax=27.52 ). CCDC registration number 1998261.
Ethyl-4-(((4-phenylureido)phenyl)sulphonamido)benzoate
4d:
1
57% yield. H NMR (400 MHz, DMSO-d6) δ: 10.47 s, 1H, NH; 7.58 d,
Starting from ethyl-4-((4-aminophenyl)sulphonamido)benzoate 3d
and phenyl isocyanate, the product 4d was synthesized according
to general procedure. The title compound was obtained as white
2H, ArH, (J=8.7 Hz); 7.46 m, 2H, ArH,); 7.25 d, 2H, ArH, (J=8.7 Hz);
6.56 m, 2H, ArH; 6.06 s, 2H, NH2, ppm. 13C NMR (100 MHz, DMSO-d6)
δ: 153.7; 142.8; 129.3; 126.8 (q, J=3.8 Hz); 124.7 (q, J=271.4 Hz);
124.2; 123.4 (q, J=32.2 Hz); 118.5; 113.1 ppm. 19F NMR (100 MHz,
DMSO-d6) δ: À 60.36 ppm. IR vmax/cmÀ 1 3423; 3347; 3249; 2937;
2869; 1619; 1593; 1520. HRMS calcld. [C13H11 F3N2O2S]+ 317.0566;
found m/z 317.0563 [M+H]+.
1
powder, in 34% yield. H NMR (400 MHz, DMSO-d6) δ: 10.70 (s 1H,
NH), 9.27 (s, 1H, NH), 8.93 (s, 1H, NH), 7.81 (d, 2H, ArH, J=8.7 Hz),
7.72 (d, 2H, ArH, J =8.9 Hz), 7.58 (d, 2H, ArH, J=8.9 Hz), 7.41 (d, 2H,
ArH, J=8.6 Hz), 7.27 (t, 2H, ArH, J=7.2 Hz), 7.20 (d, 2H, ArH, J=
8.7 Hz), 6.98 (t, 1H, ArH, J=6.9 Hz), 4.23 (q, 2H, CH2, J=7.08 Hz),
1.26 (t, CH3, 3H, J=7.09 Hz) ppm. 13C NMR (100 MHz, DMSO-d6) δ:
165.6; 152.6; 144.6; 143.1; 139.6; 131.6; 130.9; 129.2; 128.5; 124.8;
122.7; 118.8; 118.5; 118.0; 60.9; 14.6 ppm. IR vmax/cmÀ 1 3382; 3352;
3140; 3063; 2950; 1709; 1690; 1649; 1592; 1546. HRMS calcld.
[C22H21N3O5S+H]+ 440.1275; found m/z 440.1276 [M+H]+. Mp.:
N-(4-methoxyphenyl)-4-(phenylureido)benzene
sulphonamide
4a: Starting from N-(4-methoxyphenyl)-4-aminobenzene sulphona-
mide 3a and phenyl isocyanate, the product 4a was synthesized
according to general procedure. The title compound was obtained
1
as white powder, in 25% yield. H NMR (400 MHz, DMSO-d6) δ: 9.74
°
133.4–134.8 C.
(s, 1H, NH), 9.05 (s, 1H, NH), 8.78 (s, 1H, NH), 7.56 (m, 4H, ArH), 7.43
(d, 2H, ArH, J=8.0 Hz), 7.27 (m, 2H, ArH), 6.98 (m, 3H, ArH), 6.79 (d,
2H, ArH, J=8.0 Hz), 3.66 (s, 3H, OCH3), ppm. 13C NMR (100 MHz,
DMSO-d6) δ: 156.3; 152.1; 143.5; 139.2; 131.6; 130.3; 128.8; 128.6;
123.3; 122.3; 118.5; 117.4; 114.2; 55.1 ppm. IR vmax/cmÀ 1 3323; 3241;
N-((4-trifluoromethyl)phenyl)-4-(phenylureido)benzene sulphona-
mide 4e: Starting from N-((4-trifluoromethyl)phenyl)-4-aminoben-
zene sulphonamide 3e and phenyl isocyanate, the product 4e was
synthesized according to general procedure. The title compound
3114; 3043; 2958; 1662; 1591; 1542. HRMS calcld. [C20H19N3O4S+H]+
1
was obtained as off-white powder, in 74% yield. H NMR (400 MHz,
+
°
398.1169; found m/z 398.1160 [M+H] . Mp: 157–158.9 C. X-ray
DMSO-d6) δ: 10.75 (s, 1H, NH); 9.26 (s, 1H, NH); 8.91 (s, 1H, NH); 7.74
(d, 2H, ArH, J=8.9 Hz); 7.61 (m, 4H, ArH); 7.44 (d, 2H, ArH, J=
8.6 Hz); 7.31–7.27 (m, 4H, ArH); 6.99 (t, 1H, ArH, J=7.3 Hz) ppm. 13C
NMR (100 MHz, DMSO-d6) δ: 155.8;153.5; 142.3; 141.2; 139.7; 128.9;
127.3; 126.2 (q, J=271.5 Hz); 125.3 (q, J=3.8 Hz); 121.6; 119.9;
118.6; 114.8 (q, J=32.2 Hz) ppm. 19F NMR (100 MHz, DMSO-d6) δ:
À 60.31 ppm. IR 3375; 3292; 3137; 3070; 2953; 1687; 1592; 1544.
HRMS calcld. [C20H16F3N3O3S+H]+ 436.0937; found m/z 436.0936
[M+H]+.
data: monoclinic system, space group P21/n, a=9.2151(4), b=
7.2549(3), c=28.0455(11) Å, β=90.111(2) , Z=4, V= 1875.0(1) Å3,
Dc=1.44 g.cm-3, μ(Mo Kα)=0.205 mm-1, T=120 K, crystal dimen-
sions of 0.06×0.32×0.44 mm, colourless prism. The structure
converged to the final R=0.0499 and Rw=0.1175 using 7407
°
°
independent reflections for 329 refined parameters (θmax=37.10 ).
CCDC registration number 1998263.
N-phenyl-4-(phenylureido)benzene sulphonamide 4b: Starting
from N-phenyl-4-aminobenzene sulphonamide 3b and phenyl
isocyanate, the product 4b was synthesized according to general
procedure. The title compound was obtained as white powder, in
N-(4-metoxyphenyl)-4-(3,5-bis(trifluoromethyl)phenylureido)
benzene sulphonamide 4f: Starting from N-(4-methoxyphenyl)-4-
aminobenzene sulphonamide 3a and 3,5-bis(trifluoromethyl)phenyl
isocyanate, the product 4f was synthesized according to general
procedure. The title compound was obtained as white powder, in
1
22% yield. H NMR (400 MHz, DMSO-d6) δ: 10.12 (s 1H, NH), 9.09 (s
1H, NH), 8.80 (s 1H, NH), 7.65 (d, 2H, ArH, (J=8.9 Hz)), 7.56 (d, 2H,
ArH, (J=8.9 Hz)), 7.43 (d, 2H, ArH, (J=8.4 Hz), 7.27 (dd, 2H, ArH,
(J1 =8.5 Hz, J2 =7.3 Hz)), 7.22 (dd, 2H, ArH, (J1 =8.5 Hz, J2 =7.3 Hz)),
7.08 (d, 2H, ArH, (J=8.4 Hz)), 7.02–6.97 (m, 2H, ArH) ppm. 13C NMR
(100 MHz, DMSO-d6) δ: 152.6; 144.2; 139.6; 138.4; 132.1; 129.5;
129.3; 128.5; 124.3; 122.7; 120.3; 118.9; 118.0 ppm. IR vmax/cmÀ 1
3342; 3272; 3108; 3037; 1661; 1589; 1546. HRMS calcld.
[C19H17N3O3S+H]+ 368.1063; found m/z 368.1057 [M+H]+. Mp:
1
45% yield. H NMR (400 MHz, DMSO-d6) δ: 9.76 (s, 1H, NH); 9.49 (s,
1H, NH); 9.39 (s, 1H, NH); 8.17–8.13 (m, 3H, ArH); 7.68 (d, 2H, ArH, J=
12.4 Hz); 7.60 (s, 2H, ArH); 6.97 (d, 2H, ArH, J=8.9 Hz); 6.79 (d, 2H,
ArH J=8.9 Hz); 3.66 (s, 3H, CH3) ppm. 13C NMR (100 MHz, DMSO-d6)
δ: 156.9; 152.6; 143.4; 141.9; 132.9; 131.2 (q, J=32.6 Hz); 130.7;
128.4; 123.8; 123.7 (q, J=273.1 Hz); 118.7 (q, J=3.4 Hz); 118.6;
115.3 m; 114.7; 55.6 ppm. 19F NMR (100 MHz, DMSO-d6): δ:
À 61.66 ppm. IR vmax/cmÀ 1 3370; 3244; 3134; 2837; 1712; 1596; 1570;
°
169–170 C.
1543. HRMS calcld. [C22H17F6N3O4S+H]+ 534.0916; found m/z
N-(4-fluorophenyl)-4-(phenylureido)benzene sulphonamide 4c:
Starting from N-(4-fluorophenyl)-4-aminobenzene sulphonamide 3c
and phenyl isocyanate, the product 4c was synthesized according
to general procedure. The title compound was obtained as white
+
°
534.0917[M+H] . Mp.: 168.7 - 170.3 C. X-ray data: triclinic system,
space group P-1, a=9.8562(5), b=16.2616(8), c=16.4758(8) Å, α=
73.548(2), β=102.026(2), γ=85.932(2) , Z=2, V=2523.9(2) Å3,
Dc=1.52 g.cm-3, μ(Cu Kα)=1.93 mm-1, T=120 K, crystal dimen-
°
ChemPlusChem 2020, 85, 1401–1411
1409
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim