M.A.M.S. El-Sharief et al. / Journal of Fluorine Chemistry 132 (2011) 596–611
607
7.27–7.20 (m, 2H), 2.42 (s, 3H); 13C NMR (CDCl3, 100 MHz)
(C55S), 162.8 (d, J = 250.6 Hz, C–F), 153.2 (C55O), 152.8 (C55O), 139.4
(C), 130.1 (CH), 129.2 (d, J = 8.8 Hz, CH), 127.9 (d, J = 3.1 Hz, C–N),
127.6 (C–N), 125.6 (CH), 116.7 (d, J = 23.4 Hz, CH), 21.2 (CH3); 19
d
182.4
400 MHz)
2H), 7.24–7.17 (m, 2H), 7.05 (d, J = 9.0 Hz, 2H), 3.81 (s, 3H, OMe);
13C NMR (CDCl3, 100 MHz)
181.6 (C55S), 162.1 (d, J = 248.8 Hz, C–
d 9.55 (s, 1H, NH), 7.60–7.53 (m, 2H), 7.37 (d, J = 9.0 Hz,
d
F
F), 160.3 (C–O), 154.1 (C55O), 153.9 (C55N), 128.3 (d, J = 8.8 Hz, CH),
128.2 (CH), 127.9 (d, J = 3.2 Hz, C–N), 125.2 (C–N), 116.3 (d,
(CDCl3, 376.5 MHz)
d
ꢀ109.9.
J = 23.2 Hz, CH), 114.8 (CH), 55.5 (CH3); 19F (CDCl3, 376.5 MHz)
ꢀ112.1.
d
4.1.13. 1-(4-Fluorophenyl)-3-(4-methoxyphenyl)-5-
thioxoimidazolidine-2,4-dione (7b)
Mp 194–196 8C; IR (KBr):
1115 (C55S) cmꢀ1; 1H NMR (DMSO, 400 MHz)
7.47–7.39(m, 4H), 7.10(d,J = 9.0 Hz, 2H), 3.81(s, 3H, OMe);13CNMR
(DMSO, 100 MHz) 185.2 (C55S), 162.3 (d, J = 247.2 Hz, C–F), 159.6
n
1746 (C55O), 1254 (C–O), 1163 (C–O),
4.1.19. 1-(4-Ethoxyphenyl)-3-(4-fluorophenyl)-4-imino-5-
d
7.61–7.54 (m, 2H),
thioxoimidazolidin-2-one (10d)
Mp 175–176 8C; IR (KBr):
(C55N), 1256 (C–O), 1177 (C–O), 1115 (C55S) cmꢀ1
(CDCl3, 400 MHz) 9.55 (s, 1H, NH), 7.60–7.53 (m, 2H), 7.36 (d,
n
3462 (NH), 1775 (C55O), 1665
d
;
1H NMR
(C–O), 154.2 (C55O), 153.8 (C55O), 130.3 (d, J = 8.8 Hz, CH), 129.3 (d,
J = 3.0 Hz, C–N), 128.4 (CH), 123.5 (C–N), 116.6 (d, J = 23.2 Hz, CH),
d
J = 9.1 Hz, 2H), 7.25–7.17 (m, 2H), 7.03 (d, J = 9.1 Hz, 2H), 4.09 (q,
J = 7.0 Hz, 2H), 1.45 (t, J = 7.0 Hz, 3H); 13C NMR (CDCl3, 100 MHz)
114.7 (CH), 55.7 (CH3); 19F (DMSO, 376.5 MHz)
d
ꢀ112.2.
d
181.6 (C55S), 162.1 (d, J = 249.5 Hz, C–F), 159.7 (C–O), 154.2
4.1.14. 1-(4-Fluorophenyl)-3-(4-(methylthio)phenyl)-5-
(C55O), 153.9 (C55N), 128.3 (d, J = 8.8 Hz, CH), 128.2 (CH), 128.0
(d, J = 3.3 Hz, C–N), 125.0 (C–N), 116.3 (d, J = 22.7 Hz, CH), 115.2
thioxoimidazolidine-2,4-dione (7c)
Mp 166–168 8C; IR (KBr):
NMR (DMSO, 400 MHz) 7.54–7.48 (m, 2H), 7.46–7.36 (m, 6H),
2.51 (s, 3H); 13C NMR (CDCl3, 100 MHz)
181.4 (C55S), 162.7 (d,
n
1749 (C55O), 1096 (C55S) cmꢀ1
;
1H
(CH), 63.8 (CH2), 14.7 (CH3); 19F (CDCl3, 376.5 MHz)
d
ꢀ112.1;
d
MS (m/z, %) 343 (100, M+), 179 (42, p-EtO-C6H4ꢃNCS), 151 (87),
d
111 (98).
J = 250.1 Hz, C–F), 154.0 (C55O), 153.6 (C55O), 139.8 (C–S), 129.1 (d,
J = 8.8 Hz, CH), 128.6 (C–N), 128.5 (d, J = 3.0 Hz, C–N), 126.9 (CH),
126.7 (CH), 116.6 (d, J = 23.5 Hz, CH), 15.6 (CH3); 19F (CDCl3,
4.1.20. 1-(3,4-Dimethoxyphenyl)-3-(4-fluorophenyl)-4-imino-5-
thioxoimidazolidin-2-one (10e)
376.5 MHz)
d
ꢀ110.1; MS (m/z, %) 346 (19, M+), 165 (100, p-
Mp 192–194 8C; IR (KBr):
(C55N), 1215 (C–O), 1165 (C–O), 1130 (C55S) cmꢀ1; 1H NMR (DMSO,
400 MHz) 9.73 (s, 1H, NH), 7.64–7.57 (m, 2H), 7.41–7.33 (m, 3H),
6.77 (d, J = 2.5 Hz, 1H), 6.69 (dd, J = 8.8, 2.5 Hz, 1H), 3.83 (s, 3H,
OMe), 3.77 (s, 3H, OMe); 13C NMR (DMSO, 100 MHz)
182.9 (C55S),
n 3455 (NH), 1769 (C55O), 1667
CH3SꢃC6H4ꢃNCO), 153 (46, p-FꢃC6H4ꢃNCS).
d
4.1.15. 3-Benzyl-1-(4-fluorophenyl)-5-thioxoimidazolidine-2,4-
dione (7d)
d
Mp 138–140 8C; IR (KBr):
NMR (CDCl3, 400 MHz) 7.52–7.46 (m, 2H), 7.42–7.32 (m, 5H),
7.24–7.17 (m, 2H), 4.89 (s, 2H); 13C NMR (CDCl3, 100 MHz)
182.9
n
1736 (C55O), 1088 (C55S) cmꢀ1
;
1H
161.3 (d, J = 245.6 Hz, C–F), 161.7 (C–O), 155.6 (C–O), 153.9 (C55O),
153.5 (C55N), 130.0 (CH), 129.4 (d, J = 8.8 Hz, CH), 128.6 (d,
J = 2.9 Hz, C–N), 115.9 (d, J = 23.0 Hz, CH), 114.1 (C–N), 105.6 (CH),
d
d
(C55S), 162.7 (d, J = 251.0 Hz, C–F), 154.0 (C55O), 153.4 (C55O), 134.4
(C), 129.2 (CH), 129.1 (d, J = 8.8 Hz, CH), 129.0 (CH), 128.7 (CH),
99.4 (CH), 56.0 (CH3), 55.6 (CH3); 19F (DMSO, 376.5 MHz)
MS (m/z, %) 359 (44, M+), 191 (40), 111 (100).
d
ꢀ112.9;
127.8 (d, J = 3.6 Hz, C–N), 116.6 (d, J = 23.5 Hz, CH), 43.9 (CH2); 19
F
(CDCl3, 376.5 MHz)
d
ꢀ110.1.
4.1.21. 1-(4-Chlorophenyl)-3-(4-fluorophenyl)-4-imino-5-
thioxoimidazolidin-2-one (10f)
4.1.16. 1-(4-Fluorophenyl)-5-imino-3-phenyl-4-thioxoimidazolidin-
Mp 146–148 8C; IR (KBr):
(C55N), 1117 (C55S) cmꢀ1; 1H NMR (CDCl3, 400 MHz)
NH), 7.59–7.50 (m, 4H), 7.43 (d, J = 8.8 Hz, 2H), 7.26–7.18 (m, 2H);
13C NMR (CDCl3, 100 MHz)
181.0 (C55S), 162.2 (d, J = 250.2 Hz, C–
n
3430 (NH), 1771 (C55O), 1668
2-one (10a)
d
9.59 (s, 1H,
Mp 185–187 8C; IR (KBr):
(C55N), 1126 (C55S) cmꢀ1; 1H NMR (CDCl3, 400 MHz)
NH), 7.61–7.43 (m, 7H), 7.28–7.18 (m, 2H); 13C NMR (CDCl3,
100 MHz) 181.3 (C55S), 162.1 (d, J = 249.9 Hz, C–F), 154.1 (C55O),
n
3447 (NH), 1775 (C55O), 1667
d
9.57 (s, 1H,
d
F), 153.9 (C55O), 153.5 (C55N), 135.7 (C–Cl), 131.0 (C–N), 129.8 (CH),
128.4 (CH), 128.4 (d, J = 8.8 Hz, CH), 127.7 (d, J = 2.9 Hz, C–N), 116.4
d
153.7 (C55N), 132.7 (C–N), 129.8 (CH), 129.5 (CH), 128.4 (d,
J = 8.8 Hz, CH), 127.9 (d, J = 3.0 Hz, C–N), 127.1 (CH), 116.4 (d,
(d, J = 22.7 Hz, CH); 19F (CDCl3, 376.5 MHz)
333 (29, M+), 169 (100, p-Cl-C6H4ꢃNCS).
d
ꢀ111.8; MS (m/z, %)
J = 23.5 Hz, CH); 19F (CDCl3, 376.5 MHz)
d
ꢀ112.0; MS (m/z, %) 301
(7, M++2), 300 (22, M++1), 299 (99, M+), 298 (20, M+ꢀ1), 162 (37,
C6H5ꢃCNHꢃNCS), 137 (24, p-F-C6H4ꢃNCO), 135 (100, C6H5ꢃNCS).
4.1.22. 1-(4-Bromophenyl)-3-(4-fluorophenyl)-4-imino-5-
thioxoimidazolidin-2-one (10g)
Mp 200–202 8C; IR (KBr):
(C55N), 1119 (C55S) cmꢀ1; 1H NMR (DMSO, 400 MHz)
NH), 7.80 (d, J = 8.8 Hz, 2H), 7.64–7.57 (m, 2H), 7.51 (d, J = 8.8 Hz,
2H), 7.42–7.35 (m, 2H); 13C NMR (DMSO, 100 MHz)
182.8 (C55S),
n
3460 (NH), 1773 (C55O), 1667
4.1.17. 1-(4-Fluorophenyl)-5-imino-4-thioxo-3-p-tolylimidazolidin-
d
9.71 (s, 1H,
2-one (10b)
Mp 176–178 8C; IR (KBr):
(C55N), 1113 (C55S) cmꢀ1; 1H NMR (DMSO, 400 MHz)
NH), 7.64–7.57 (m, 2H), 7.41–7.33 (m, 6H), 2.37 (CH3); 13C NMR
(DMSO, 100 MHz) 183.0 (C55S), 161.5 (d, J = 246.2 Hz, C–F), 154.4
n
3462 (NH), 1771 (C55O), 1668
d
d
9.63 (s, 1H,
161.6 (d, J = 245.5 Hz, C–F), 154.3 (C55O), 153.7 (C55N), 132.8 (C–N),
132.6 (CH), 130.1 (CH), 129.7 (d, J = 8.8 Hz, CH), 128.9 (d, J = 2.9 Hz,
C–N), 122.9 (C–Br), 116.1 (d, J = 22.7 Hz, CH); 19F (DMSO,
d
(C55O), 154.0 (C55N), 139.4 (C), 130.9 (C–N), 129.9 (CH), 129.7 (d,
J = 8.8 Hz, CH), 129.0 (d, J = 3.0 Hz, C–N), 127.6 (CH), 116.0 (d,
376.5 MHz)
(99, p-F-C6H4ꢃNCNH), 90 (100).
d
ꢀ113.0; MS (m/z, %) 377 (43, M+), 212 (86), 136
J = 22.8 Hz, CH), 21.0 (CH3); 19F (DMSO, 376.5 MHz)
d
ꢀ113.1; MS
(m/z, %) 314 (16, M++1), 313 (74, M+), 312 (15, M+ꢀ1), 149 (94, p-
CH3ꢃC6H4ꢃNCS), 137 (24, p-F-C6H4ꢃNCO), 135 (100, C6H5ꢃNCS), 91
(100, C6H4ꢃCH3+).
4.1.23. 1-(2-Fluorophenyl)-4-imino-3-phenyl-5-thioxoimidazolidin-
2-one (10h)
Mp 130–134 8C; IR (KBr):
(C55N), 1096 (C55S) cmꢀ1; 1H NMR (CDCl3, 400 MHz)
NH), 7.56–7.40 (m, 7H), 7.31–7.21 (m, 2H); 13C NMR (CDCl3,
100 MHz) 181.4 (C55S), 157.7 (d, J = 253.1 Hz, C–F), 153.5 (C55O),
n
3435 (NH), 1782 (C55O), 1672
d
9.51 (s, 1H,
4.1.18. 1-(4-Fluorophenyl)-5-imino-3-(4-methoxyphenyl)-4-
thioxoimidazolidin-2-one (10c)
d
Mp 168–170 8C; IR (KBr):
n
3455 (NH), 1778 (C55O), 1667
153.0 (C55N), 132.6 (C), 131.3 (d, J = 8.0 Hz, CH), 129.7 (d, J = 7.4 Hz,
CH), 129.4 (CH), 127.0 (CH), 124.8 (d, J = 3.6 Hz, CH), 119.4
(C55N), 1254 (C–O), 1177 (C–O), 1113 (C55S) cmꢀ1; 1H NMR (CDCl3,