Vol. 27, No. 8 (2015)
Synthesis and Antibacterial Activity of 1,5-Disubstituted Indolin-2-one Derivatives 2961
1484, 1378, 1335, 1170, 1128, 1106, 1026, 953, 932, 837,
810, 599, 513. HR-MS (ESI): Calcd for C14H8N2O3SCl4 [M-H]-:
424.8903; found: 424.8905.
3,3-Dichloro-N-(4-methoxyphenyl))-2-oxoindoline-5-
sulfonamide (6d): Synthesize as compound 6a, yellowish
1
solid, yield: 88 %; m.p.: 188-189 °C. H NMR (400 MHz,
Synthesis of 1-decyl-2,3-dioxoindoline-5-sulfonyl
chloride (5): 1-Decylindoline-2,3-dione (5.74 g, 20 mmol)
was added in portions into chlorosulfonic acid (23.2 g, 200
mmol) in CH2Cl2 (20 mL) below 5 °C. The reaction mixture
was stirred for another 0.5 h at the same temperature and then
the reaction temperature was slowly raised to reflux and main-
tained for 3 h. After recycled the solvent, the mixture was
cooled and poured into ice, standed still 0.5 h in the ice water,
filtrated and the solid was washed with cold water, dried in
vacuum oven to afford 5 (6.34 g, 86.6 %). Yellow solid, m.p.:
103-104 °C. 1H NMR (400 MHz, CDCl3, TMS): δ 8.29 (dd,
J = 8.4, 2.1 Hz, 1H), 8.27 (d, J = 1.8 Hz, 1H), 7.14 (d, J = 8.4
Hz, 1H), 3.83 (t, J = 7.6, 2H), 1.78-1.70 (m, 2H), 1.40-1.19
(m, 14H), 0.90 (t, J = 6.8 Hz, 3H). IR (KBr, νmax, cm-1): 3484,
3098, 2921, 2850, 1748, 1604, 1478, 1374, 1336, 1177, 1128,
1064, 842, 727, 635, 607, 534, 510. HR-MS (ESI): Calcd for
C18H24NO4SCl [M + Na]+: 408.1013; found: 408.1015.
Synthesis of 3,3-dichloro-N-(4-hydroxyphenyl)-2-
oxoindoline-5-sulfonamide (6a): 4-Aminophenol (0.92 g,
8.40 mmol) was added to the solution of 3,3-dichloro-2-
oxoindoline-5-sulfuryl chloride (1.20 g, 4 mmol) in THF (20
mL) at room temperature. The reaction mixture was heated to
reflux and maintained for 3 h, then cooled to room temperature
and evaporated under reduced pressure to remove the excess
solvent, After acidification with 50 mL 10 % cold hydrochloric
acid, the mixture was extracted with ethyl acetate. The organic
layer was washed with 10 % hydrochloric acid, brine, dried
and evaporated to give crude product. The crude product was
chromatographed using petroleum ether and ethyl acetate as
eluent to afford the target products 6a, yellowish solid, yield:
CDCl3, TMS) : δ = 9.17 (s, 1H), 7.87 (d, J = 1.1 Hz, 1H), 7.73
(dd, J = 8.2, 1.0 Hz, 1H), 7.02 (m, 4H), 6.78 (d, J = 8.9 Hz,
2H), 3.74 (s, 3H). IR (KBr, νmax, cm-1): 3252, 1759, 1614, 1506,
1341, 1238, 1155, 836, 723, 521. HR-MS (ESI): Calcd for
C15H12N2O4SCl2 [M-H]-: 384.9817; found: 384.9811.
N-(4-Aminophenyl)-3,3-dichloro-2-oxoindoline-5-
sulfonamide (6e): Synthesize as compound 6a, deep yellow
1
solid, yield: 18 %; m.p.: > 260 °C. H NMR (400 MHz, d6-
DMSO, TMS): δ = 11.81 (s, 1H), 9.74 (s, 1H), 7.82 (d, J = 1.7
Hz, 1H), 7.68 (dd, J = 8.3, 1.7 Hz, 1H), 7.10 (d, J = 8.3 Hz,
1H), 6.81 (d, J = 8.3 Hz, 2H), 6.63 (s, 2H). IR (KBr, νmax
,
cm-1): 3431, 2928, 1748, 1618, 1509, 1468, 1403, 1150, 1118,
1079, 844, 617, 514. HR-MS (ESI): Calcd for C14H11N3O3SCl2
[M-H]-: 369.9820; found: 369.9816.
3,3-Dichloro-N-(4-chlorophenyl)-2-oxoindoline-5-
sulfonamide (6f): Synthesize as compound 6a, pale yellow
1
solid, yield: 92 %; m.p.: 205-206 °C. H NMR (400 MHz,
CDCl3, TMS): δ = 8.63 (s, 1H), 7.94 (s, 1H), 7.74 (d, J = 8.9
Hz, 1H), 7.25 (d, J = 9.0 Hz, 2H), 7.08-6.99 (m, 3H), 6.90 (s,
1H). IR (KBr, νmax, cm-1): 3219 , 1741, 1620, 1491, 1388, 1314,
1294, 1141, 1076, 949, 840, 711, 514. HR-MS (ESI): Calcd
for C14H9N2O3SCl3 [M-H]-: 388.9321; found: 388.9328.
3,3-Dichloro-N-(4-chlorophenyl)-1-ethyl-2-oxoin-
doline-5-sulfonamide (7a): Synthesize as compound 6a,
1
yellowish solid, two step yield: 66 %; m.p.: 193-194 °C. H
NMR (400 MHz, CDCl3, TMS) δ 7.94 (d, J = 1.3 Hz, 1H),
7.77 (dd, J = 8.3, 1.4 Hz, 1H), 7.27 (d, J = 1.4 Hz, 1H), 7.25
(s, 1H), 7.04 (d, J = 8.6 Hz, 2H), 6.92 (d, J = 8.4 Hz, 1H), 6.50
(s, 1H), 3.80 (q, J = 7.2 Hz, 2H), 1.31 (t, J = 7.2 Hz, 3H). IR
(KBr, νmax, cm-1): 3310 , 1738, 1606, 1488, 1335, 1155,
1111,1064, 917, 831, 614, 590, 522. HR-MS (ESI): Calcd for
C16H13N2O3SCl3 [M-H]-: 416.9634; found: 416.9634.
1
73 %; m.p.: 195-196 °C. H NMR (400 MHz, d6-DMSO,
TMS): δ = 11.78 (s, 1H), 9.71 (s, 1H), 9.35 (s, 1H), 7.79 (d,
J = 1.6 Hz, 1H), 7.66 (dd, J = 8.3, 1.8 Hz, 1H), 7.09 (d, J = 8.3
Hz, 1H), 6.84 (d, J = 8.8 Hz, 2H), 6.62 (d, J = 8.8 Hz, 2H). IR
(KBr, νmax, cm-1): 3375, 3193(w) , 1765, 1739, 1615, 1509,
1474, 1386, 1324, 1209, 1147, 1124, 1071, 962, 841, 714,
591, 523. HR-MS (ESI): Calcd for C14H10N2O4SCl2 [M-H]-:
370.9660; found: 370.9660.
3,3-Dichloro-1-ethyl-N-(4-hydroxyphenyl)-2-oxoindo-
line-5-sulfonamide (7b): Synthesize as compound 6a, yellowish
solid, two step yield: 30 %; m.p.: 203-204 °C. 1H NMR (400
MHz, d6-DMSO, TMS): δ = 9.76 (s, 1H), 9.35 (s, 1H), 7.85
(d, J = 1.8 Hz, 1H), 7.74 (dd, J = 8.4, 1.8 Hz, 1H), 7.40 (d, J =
8.4 Hz, 1H), 6.86 (d, J = 8.8 Hz, 2H), 6.62 (d, J = 8.8 Hz, 2H),
3.79 (q, J = 7.2 Hz, 2H), 1.17 (t, J = 7.1 Hz, 3H). IR (KBr,
3,3-Dichloro-N-(4-fluorophenyl)-2-oxoindoline-5-
sulfonamide (6b): Synthesize as compound 6a, yellowish
ν
max, cm-1): 3514 , 3296, 1736, 1609, 1506, 1409, 1333, 1150,
1112, 1071, 841, 611, 520. HR-MS (ESI): Calcd for
1
solid, yield: 93 %; m.p.: 207-208 °C. H NMR (400 MHz,
CD3COCD3, TMS): δ = 10.50 (s, 1H), 8.98 (s, 1H), 7.90 (s,
1H), 7.77 (d, J = 8.3 Hz, 1H), 7.25 -7.17 (m, 3H), 7.07 (t, J =
8.6 Hz, 2H). IR (KBr, νmax, cm-1): 3271, 1747 , 1614, 1504,
1471, 1391, 1345, 1144, 1127, 1074, 838, 723, 602, 504. HR-
MS (ESI): Calcd for C14H9N2O3SCl2F [M-H]-: 372.9617;
found: 372.9615.
C16H14N2O4SCl2 [M-H]-: 398.9973, found: 398.9965.
3,3-Dichloro-N-(4-chlorophenyl)-1-[(2-chloropyridin-
4-yl)methyl]-2-oxoindoline-5-sulfonamide (7c): Synthesize
as compound 6a, yellowish solid, two step yield: 40 %; m.p.:
205-206 °C. 1H NMR (400 MHz, CDCl3, TMS): δ = 8.41 (d,
J = 2.3 Hz, 1H), 7.98 (d, J = 1.7 Hz, 1H), 7.74 (dd, J = 8.3, 1.8
Hz, 1H), 7.60 (dd, J = 8.3, 2.5 Hz, 1H), 7.37 (d, J = 8.2 Hz,
1H), 7.27 (d, J = 8.7 Hz, 2H), 7.06 (d, J = 8.7 Hz, 2H), 6.82
3,3-Dichloro-N-(4-nitrophenyl)-2-oxoindoline-5-
sulfonamide (6c): Synthesize as compound 6a, yellowish solid,
1
yield: 30 %; m.p.: 201-202 °C. H NMR (400 MHz, CDCl3,
(d, J = 8.3 Hz, 1H), 6.69 (s, 1H), 4.95 (s, 2H). IR (KBr, νmax,
TMS) : δ = 9.72 (s, 1H), 8.12-8.03 (m, 2H), 7.97 (d, J = 10.0 Hz,
1H), 7.87 (t, J = 7.7 Hz, 2H), 7.66 (t, J = 7.8 Hz, 1H), 7.22 (d, J
= 7.9 Hz, 1H), 7.00 (d, J = 8.4 Hz, 1H). IR (KBr, νmax, cm-1):
3369, 3266, 1764, 1603, 1531, 1481, 1388, 1340, 1265, 1147,
1070, 957, 914, 844, 631, 594. HR-MS (ESI): Calcd for
C14H9N3O5SCl2 [M-H]-: 399.9562; found: 399.9564.
cm-1): 3440(w) , 3211, 1739, 1612, 1486, 1339, 1150, 912,
835, 720, 597, 523. HR-MS (ESI): Calcd for C20H13N2O4SCl4
[M-H]-: 515,9324; found: 515,9324.
3,3-Dichloro-1-[(2-chloropyridin-4-yl)methyl]-N-(4-
hydroxyphenyl)-2-oxoindoline-5-sulfonamide (7d): Synthe-
size as compound 6a, yellowish solid, two step yield: 46 %;