2800
A. Shiri, A. Khoramabadi-zad
PAPER
Tetrachlorodimethylglycoluril (2b)
Yield: 286 mg (93%); white solid.
stirred at r.t. for 1 h. Then the solid was collected by filtration,
washed with H2O, and dried.
IR (Nujol): 1767, 1747, 1344, 1160, 730 cm–1.
Yield: 177 mg (98%); white solid; mp 180–182 °C.
1H NMR (90 MHz, CDCl3): d = 1.86 (s, CH3).
IR (Nujol): 3093, 1787, 1741, 1714, 1302, 1270, 1172, 1076, 701
cm–1.
Anal. Calcd for C6H6Cl4N4O2: C, 23.4; H, 2.0; N, 18.2. Found: C,
24.2; H, 2.2; N, 18.3.
1H NMR (90 MHz, CDCl3): d = 7.73–7.97 (m, Harom).
Tetrachlorodiethylglycoluril (2c)
Yield: 300 mg (91%); white solid.
N-Chlorosuccinimide
A suspension of succinimide (0.59 g, 6 mmol) in H2O (4 mL) and
glacial AcOH (2 mL) was treated with TCCA (0.468 g, 2.0 mmol)
and stirred at r.t. for 1 h. Then the product was extracted with CHCl3
(3 × 10 mL), and the soln was dried (MgSO4), filtered, and evapo-
rated.
IR (Nujol): 1781, 1769, 1330, 1142, 794, 727 cm–1.
1H NMR (90 MHz, CDCl3): d = 1.07 (t, J = 7.5 Hz, 3 H, CH3), 2.40
(q, J = 7.5 Hz, 2 H, CH2).
13C NMR (23 MHz, CDCl3): d = 7.11, 22.60, 86.42, 154.40.
Yield: 126 mg (95%); colorless crystalline solid; mp 151–152 °C.
IR (Nujol): 1713, 1328, 1296, 1159, 961, 651 cm–1.
1H NMR (90 MHz, CDCl3): d = 2.88 (s, CH2).
Anal. Calcd for C8H10Cl4N4O2: C, 28.6; H, 3.0; N, 16.6. Found: C,
29.0; H, 3.0; N, 16.0.
Tetrachlorodiphenylglycoluril (Iodogen, 2d)
Yield: 393 mg (96%); white solid.
N,N¢-Dichlorophenobarbital
A suspension of phenobarbital (0.232 g, 1mmol) in H2O (10 mL)
was treated with TCCA (0.176 g, 0.76 mmol) for 1 h at r.t. Then the
solid was filtered, washed with H2O, dried, and recrystallized from
CHCl3 to give the pure product.
IR (Nujol): 3054, 1782, 1770, 1331, 1143, 707 cm–1.
1H NMR (90 MHz, acetone-d6): d = 6.97–7.30 (m, Harom).
Anal. Calcd for C16H10Cl4N4O2: C, 44.4; H, 2.3; N, 12.9. Found: C,
44.9; H, 2.3; N, 12.7.
Yield: 267 mg (89%); white solid; mp 147–150 °C.
IR (Nujol): 3627, 3067, 1769, 1726, 1493, 1449, 1379, 1293, 1186,
1140, 818, 759 cm–1.
Bis(3-bromophenyl)tetrachloroglycoluril (2e)
Yield: 547 mg (93%); white solid.
1H NMR (90 MHz, CDCl3): d = 0.96 (t, J = 7.1 Hz, 3 H, CH3), 2.54
(q, J = 7.1 Hz, 2 H, CH2), 7.13–7.45 (m, 5 H, Harom).
IR (Nujol): 3095, 1790, 1769, 1571, 1241, 1153, 708 cm–1.
1H NMR (90 MHz, CDCl3): d = 6.84–7.46 (m, Harom).
N,N¢-Dichlorobarbital
Anal. Calcd for C16H8Br2Cl4N4O2: C, 32.5; H, 1.3; N, 9.5. Found:
C, 33.6; H, 1.5; N, 9.6.
Barbital (0.184 g, 1 mmol) and NaHCO3 (0.6 g, 0.0083 mmol) were
mixed in H2O (5 mL); then TCCA (0.176 g, 0.76 mmol) was added
and the mixture was allowed to stir for 1 h at r.t. The solid was fil-
tered, washed with H2O (2×), and dried.
Bis(4-bromophenyl)tetrachloroglycoluril (2f)
Yield: 560 mg (95%); white solid.
Yield: 164 mg (65%); white solid; mp 120–124 °C.
IR (Nujol): 3093, 1784, 1589, 1253, 1148, 711 cm–1.
IR (Nujol): 1777, 1718, 1580, 1352, 1145, 823, 708 cm–1.
1H NMR (90 MHz, CDCl3): d = 6.73–7.39 (2 d, J = 8.7 Hz, 4 H,
Harom).
1H NMR (90 MHz, CDCl3): d = 0.82 (t, J = 7.3 Hz, 3 H, CH3), 2.11
(q, J = 7.3 Hz, 2 H, CH2).
Anal. Calcd for C16H8Br2Cl4N4O2: C, 32.5; H, 1.3; N, 9.5. Found:
C, 33.2; H, 1.3; N, 10.1.
N-Chlorosaccharin
Saccharin (0.183 g, 1 mmol) and NaHCO3 (0.6 g, 0.0083 mmol)
were mixed in H2O (5 mL); then TCCA (0.078 g, 0.33 mmol) was
added and the mixture was allowed to stir for 24 h at r.t. The solid
was filtered, washed with H2O (2×), and dried.
Tetrachlorobis(3-chlorophenyl)glycoluril (2g)
Yield: 460 mg (92%); white solid.
IR (Nujol): 1791, 1767, 1596, 1577, 1324, 1142, 726 cm–1.
1H NMR (90 MHz, acetone-d6): d = 7.17–7.43 (m, Harom).
Yield: 130 mg (60%); white solid; mp 146–148 °C.
Anal. Calcd for C16H8Cl6N4O2: C, 38.3; H, 1.6; N, 11.1. Found: C,
38.5; H, 1.6; N, 11.1.
IR (Nujol): 3094, 1748, 1740, 1464, 1374, 1194, 956, 748, 731, 587,
576 cm–1.
1H NMR (90 MHz, CDCl3): d = 7.85–8.18 (m, Harom).
Tetrachlorobis(4-chlorophenyl)glycoluril (2h)
Yield: 475 mg (95%); white solid.
Chloramine-T
IR (Nujol): 1776,1596, 1492, 1325, 1253, 1149, 1096, 852, 812,
722 cm–1.
TCCA (0.176 g, 0.76 mmol) was added to a soln of p-toluene-
sulfonamide (0.171 g, 1 mmol) in 2 N NaOH (1 mL), and the mix-
ture was stirred for 1 h at r.t. The soln was then cooled at 0 °C and
the resulting precipitate was collected by filtration and dried.
1H NMR (90 MHz, CDCl3): d = 6.81–7.22 (2 d, J = 8.3 Hz, 4 H,
Harom).
Yield: 261 mg (93%); white crystalline solid; mp 178–180 °C.
Anal. Calcd for C16H8Cl6N4O2: C, 38.3; H, 1.6; N, 11.1. Found: C,
38.7; H, 1.7; N, 11.0.
IR (Nujol): 3512, 3156, 1682, 1251, 1132, 1085, 927, 808, 700
cm–1.
N-Chlorophthalimide
A suspension of phthalimide (0.185 g, 1 mmol) in H2O (10 mL) was
treated with TCCA (0.078 g, 0.33 mmol), and the mixture was
1H NMR (300 MHz, D2O): d = 2.23 (s, 3 H, CH3), 7.21–7.57 (2 d,
J = 8.1 Hz, 4 H, Harom).
Synthesis 2009, No. 16, 2797–2801 © Thieme Stuttgart · New York