A. Klaꢀsek et al. / Tetrahedron 63 (2007) 7059–7069
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3.2.12. 1,3-Bis[2-(1,3,5-tributyl-2-oxo-2,3-dihydro-1H-
imidazol-4-yl)-phenyl]-urea (5g). Compound was prepared
from 3g in 79% yield. Yellowish oil; IR: 3280, 2958, 2932,
2872, 1667, 1642, 1578, 1527, 1454, 1415, 1373, 1285,
Anal. calcd (found) for C53H52N6O3: C 77.53 (77.41); H
6.38 (6.51); N 10.24 (10.14).
3.2.16. 1,3-Bis[2-(1,3-dibutyl-2-oxo-5-phenyl-2,3-di-
hydro-1H-imidazol-4-yl)-phenyl]-urea (5k). Compound
was prepared from 3k in 63% yield. Colourless crystals;
mp 154–164 ꢂC; IR: 3287, 3057, 2959, 2933, 2872, 1686,
1660, 1578, 1526, 1451, 1406, 1369, 1285, 1192, 1075,
939, 873, 756, 701, 655, 629 cmꢀ1. Positive-ion APCI-
MS: m/z 753 [M+H]+ (100%), 390 [F+26]+, 364 [F]+.
Positive-ion APCI-MS/MS of m/z 753: m/z 390 [F+26]+
(100%), 364 [F]+, 334 [F+26ꢀbutene]+, 278 [F+26ꢀ
2ꢃbutene]+, 235 [F+26ꢀ2ꢃbutene–NHCO]+. Negative-ion
APCI-MS: m/z 751 [MꢀH]ꢀ (100%). Negative-ion APCI-
MS/MS of m/z 751: m/z 362 [F+26ꢀ2H]ꢀ (100%), 306
[Fꢀ2H]ꢀ, 263 [F+26ꢀ2H–BuNCO]+, 206 [F+26ꢀ2H–
1192, 1113, 1062, 1038, 945, 755, 654, 629, 549 cmꢀ1
.
Positive-ion APCI-MS: m/z 713 [M+H]+, 370 [F+26]+, 344
[F]+ (100%). Positive-ion APCI-MS/MS of m/z 713: m/z
370 [F+26]+ (100%), 344 [F]+. Negative-ion APCI-MS:
m/z 711 [MꢀH]ꢀ, 342 [Fꢀ2H]ꢀ (100%).
Anal. calcd (found) for C43H64N6O3: C 72.43 (72.31); H
9.05 (9.23); N 11.79 (11.62).
3.2.13. 1,3-Bis[2-(1,5-dibutyl-2-oxo-3-phenyl-2,3-di-
hydro-1H-imidazol-4-yl)-phenyl]-urea (5h). Compound
was prepared from 3h in 16% yield besides 4h. Colourless
crystals; mp 183–187 ꢂC (hexane); IR: 3303, 3063, 2957,
2932, 2871, 1695, 1669, 1643, 1579, 1526, 1503, 1449,
1409, 1380, 1286, 1193, 1112, 945, 886, 755, 693, 651,
543, 508 cmꢀ1. Positive-ion APCI-MS: m/z 753 [M+H]+
(100%), 390 [F+26]+, 364 [F]+. Positive-ion APCI-MS/MS
of m/z 753: m/z 654 [M+HꢀBuNCO]+, 390 [F+26]+
(100%), 364 [F]+, 334 [F+26ꢀbutene]+, 278 [F+26ꢀ
2ꢃbutene]+, 235 [F+26ꢀ2ꢃbutene–NHCO]+. Negative-ion
APCI-MS: m/z 751 [MꢀH]ꢀ (100%), 362 [Fꢀ2H]ꢀ. Nega-
tive-ion APCI-MS/MS of m/z 751: m/z 362 [Fꢀ2H]ꢀ
(100%), 263 [Fꢀ2H–BuNCO]ꢀ.
ꢁ
BuNCO–Bu]+ .
Anal. calcd (found) for C47H56N6O3: C 74.97 (74.79); H
7.50 (7.68); N 11.16 (11.01).
3.2.17. 1,3-Bis[2-(1-butyl-3,5-diphenyl-2-oxo-2,3-di-
hydro-1H-imidazol-4-yl)-phenyl]-urea (5l). Compound
was prepared from 3l in 54% yield besides 4l. Colourless
crystals; mp 258–264 ꢂC (benzene); IR: 3338, 3177, 3061,
3043, 2957, 2932, 2872, 1697, 1671, 1598, 1579, 1517,
1499, 1448, 1383, 1288, 1227, 1192, 1091, 1073, 1027,
946, 806, 758, 698, 651, 632, 525, 505 cmꢀ1. Positive-ion
APCI-MS: m/z 793 [M+H]+ (100%), 410 [F+26]+, 384
[F]+. Positive-ion APCI-MS/MS of m/z 793: m/z 410
[F+26]+ (100%), 384 [F]+, 354 [F+26ꢀbutene]+, 285
[FꢀBuNCO]+, 235 [F+26ꢀbutene–PhNCO]+. Negative-
ion APCI-MS: m/z 791 [MꢀH]ꢀ (100%). Negative-ion
APCI-MS/MS of m/z 791: m/z 382 [Fꢀ2H]ꢀ (100%), 326
[Fꢀ2H–butene]ꢀ, 283 [Fꢀ2H–BuNCO]ꢀ.
Anal. calcd (found) for C47H56N6O3: C 74.97 (74.79); H
7.50 (7.67); N 11.16 (11.02).
3.2.14. 1,3-Bis[2-(1-benzyl-3,5-dibutyl-2-oxo-2,3-di-
hydro-1H-imidazol-4-yl)-phenyl]-urea (5i). Compound
was prepared from 3i in 50% yield besides 4i. Yellowish oil;
IR: 3221, 3030, 2957, 2930, 2871, 1673, 1643, 1578, 1527,
1496, 1453, 1411, 1400, 1285, 1192, 1111, 1076, 1029, 946,
785, 753, 732, 700, 654, 577, 550 cmꢀ1. Positive-ion APCI-
MS: m/z 781 [M+H]+ (100%), 404 [F+26]+, 378 [F]+. Posi-
Anal. calcd (found) for C51H48N6O3: C 77.25 (77.31); H
6.10 (6.21); N 10.60 (10.42).
ꢁ
tive-ion APCI-MS/MS of m/z 781: m/z 690 [M+HꢀBn]+ ,
648 [M+HꢀBnNCO]+, 404 [F+26]+ (100%), 378 [F]+, 360
3.2.18. 1,3-Bis[2-(1-benzyl-3-butyl-2-oxo-5-phenyl-2,3-
dihydro-1H-imidazol-4-yl)-phenyl]-urea (5m). Com-
pound was prepared from 3m in 83% yield. Colourless crys-
tals; mp 95–100 ꢂC; IR: 3331, 3231, 3190, 3060, 3030,
2957, 2932, 2871, 1687, 1667, 1579, 1526, 1497, 1450,
1401, 1359, 1285, 1226, 1195, 113, 1074, 1028, 972, 946,
919, 872, 818, 751, 700, 660, 629, 582, 552, 509 cmꢀ1. Pos-
itive-ion APCI-MS: m/z 821 [M+H]+, 424 [F+26]+, 398 [F]+
(100%). Positive-ion APCI-MS/MS of m/z 821: m/z 424
[F+26]+, 398 [F]+ (100%), 368 [F+26ꢀbutene]+, 333
ꢁ
ꢁ
[F+26ꢀNH2CO]+ , 348 [F+26ꢀbutene]+, 313 [F+26ꢀBn]+ ,
ꢁ
270 [F+26ꢀBnNHCO]+ , 245 [FꢀBnNCO]+. Negative-ion
APCI-MS: m/z 779 [MꢀH]ꢀ (100%), 376 [Fꢀ2H]ꢀ. Nega-
tive-ion APCI-MS/MS of m/z 779: m/z 376 [Fꢀ2H]ꢀ
ꢁ
(100%), 320 [Fꢀ2H–butene]ꢀ , 243 [Fꢀ2H–BnNCO]+.
Anal. calcd (found) for C49H60N6O3: C 75.35 (75.16); H
7.74 (7.82); N 10.76 (10.59).
ꢁ
3.2.15. 1,3-Bis[2-(1-benzyl-5-butyl-2-oxo-3-phenyl-2,3-
dihydro-1H-imidazol-4-yl)-phenyl]-urea (5j). Compound
was prepared from 3j in 41% yield besides 4j. Colourless
crystals; mp 110–115 ꢂC (hexane); IR: 3298, 3062, 3030,
2957, 2930, 2869, 1676, 1598, 1580, 1524, 1501, 1451,
1407, 1359, 1287, 1195, 1074, 1029, 960, 750, 697, 581,
540, 506 cmꢀ1. Positive-ion APCI-MS: m/z 821 [M+H]+
(100%), 424 [F+26]+, 398 [F]+. Positive-ion APCI-MS/MS
[F+26ꢀBn]+ , 276 [F+26ꢀBn–Bu]+, 234 [F+26ꢀBn–
ꢁ
BuNCO]+ . Negative-ion APCI-MS: m/z 819 [MꢀH]ꢀ
(100%). Negative-ion APCI-MS/MS of m/z 819: m/z 396
[Fꢀ2H]ꢀ (100%), 340 [Fꢀ2H–butene]ꢀ, 263 [Fꢀ2H–
BnNCO]+.
Anal. calcd (found) for C53H52N6O3: C 77.53 (77.38); H
6.38 (6.52); N 10.24 (10.08).
ꢁ
of m/z 821: m/z 730 [M+HꢀBn]+ , 688 [M+HꢀBnNCO]+,
424 [F+26]+ (100%), 398 [F]+, 368 [F+26ꢀbutene]+, 333
3.2.19. 1,3-Bis[2-(1-benzyl-3,5-diphenyl-2-oxo-2,3-di-
hydro-1H-imidazol-4-yl)-phenyl]-urea (5n). Compound
was prepared from 3n in 74% yield. Colourless crystals;
mp 227–232 ꢂC; IR: 3340, 3285, 3221, 3058, 3032, 2947,
1688, 1671, 1598, 1580, 1519, 1497, 1448, 1388, 1288,
ꢁ
ꢁ
[F+26ꢀBn]+ , 290 [F+26ꢀBnNHCO]+ , 265 [FꢀBnNCO]+.
Negative-ion APCI-MS: m/z 819 [MꢀH]ꢀ (100%), 396
[Fꢀ2H]ꢀ. Negative-ion APCI-MS/MS of m/z 819: m/z 396
ꢁ
[Fꢀ2H]ꢀ (100%), 305 [Fꢀ2H–Bn]ꢀ .