2320
L. Meng and D.-Q. Shi
2H, CH2), 6.95–7.13 (m, 5H, Ar-H), 7.44–.52 (m, 2H, Ar-H), 7.86 (d, J =
1
7.6 Hz, 2H, Ar-H), 7.95 (s, 1H, Tr-H), 8.32 (s, 1H, Tr-H); 31P{ H} NMR
(162 MHz) δ: 62.72; MS m/z (%): 421 (M+1, 30.4), 420 (M+, 50.4), 191
(20.2), 143 (41.6), 114 (20.6), 104 (42.5), 95 (74.8), 91 (65.4), 76 (53.8),
67 (100). Anal. Calcd. for C18H18FN4O3PS: C 51.43, H 4.32, N 13.33.
Found C 51.58, H 4.13, N 13.09.
O-(4-Fluorophenyl), O-Methyl, O-{Z-[1-Phenyl-2-(1H-1,2,4-
triazol-1-yl)ethylidene]amino} Phosphorothioate (2f)
Yellow oil, Yield: 89%; IR (KBr, cm−1) υ: 3061, 2963 (Ar-H), 1600,
1582 (C N), 1486, 1446 (Ar), 1210 (P-O-Ar), 1046 (P O C), 674 (P S);
1H NMR: δ 3.92 (d, J = 13.6 Hz, 3H, OCH3), 5.51 (s, 2H, CH2), 7.01–
1
7.87 (m, 9H, Ar-H), 7.93 (s, 1H, Tr-H), 8.23 (s, 1H, Tr-H); 31P{ H} NMR
(162 MHz) δ: 62.65; MS (70eV) m/z (%): 407 (M+, 2.2), 205 (6.6), 158
(9.2), 135 (13.3), 125 (9.1), 111 (37.6), 103 (27.6), 95 (20.0), 83 (64.2), 77
(100), 63 (36.1), 55 (84.5). Anal. Calcd. for C17H16FN4O3PS: C 50.25, H
3.97, N 13.79. Found C 50.41, H 4.13, N 13.54.
O-(4-Chlorophenyl), O-Ethyl, O-{Z-[1-Phenyl-2-(1H-1,2,4-
triazol-1-yl)ethylidene]amino} Phosphorothioate (2g)
Yellow oil, Yield: 73%; IR (KBr, cm−1) υ: 2983 (Ar-H), 1590 (C N),
1
1486, 1446 (Ar), 1209 (P-O-Ar), 1036 (P O C), 677 (P S); H NMR:
δ 1.37 (t, J = 7.2 Hz, 3H, CH2CH3), 4.25–4.38 (m, 2H, CH2CH3), 5.50
(s, 2H, CH2), 7.11 (d, J = 7.2 Hz, 2H, Ar-H), 7.29 (d, J = 8.4 Hz, 2H,
Ar-H), 7.45–7.52 (m, 3H, Ar-H), 7.85 (d, J = 7.2 Hz, 2H, Ar-H), 7.94 (s,
1
1H, Tr-H), 8.29 (s, 1H, Tr-H); 31P{ H} NMR (162 MHz) δ: 62.72; MS
m/z (%): 437 (M+1, 4.9), 223 (8.4), 205 (23.2), 185 (11.8), 159 (14.0), 127
(12.6), 105 (29.3), 104 (46.1), 99 (55.9), 97 (39.4), 77 (100), 63 (41.8),
55 (83.8). Anal. Calcd. for C18H18ClN4O3PS: C 49.49, H 4.15, N 12.83.
Found C 49.25, H 4.04, N 12.79.
O-Ethyl, O-(4-Nitrophenyl), O-{Z-[1-Phenyl-2-(1H-1,2,4-triazol-
1-yl)ethylidene]amino} Phosphorothioate (2h)
Yellow oil, Yield: 60%; IR (KBr, cm−1) υ: 3105, 2984 (Ar-H), 1532
1
(C N), 1475, 1446 (Ar), 1216 (P-O-Ar), 1035 (P O C), 676 (P S); H
NMR: δ 1.40 (t, J = 7.2 Hz, 3H, CH2CH3), 4.28–4.36 (m, 2H, CH2CH3),
5.54 (s, 2H, CH2), 7.33 (d, J = 8.0 Hz, 2H, Ar-H), 7.48–7.54 (m, 3H, Ar-
H), 7.84 (d, J = 7.2 Hz, 2H, Ar-H), 8.00 (s, 1H, Tr-H), 8.23 (d, J = 8.4 Hz,
1
2H, Ar-H), 8.47 (s, 1H, Tr-H); 31P{ H} NMR (162 MHz) δ: 62.86; MS m/z
(%): 448 (M+1, 1.8), 218 (3.6), 188 (5.4), 153 (7.1), 148 (8.1), 125 (30.3),
109 (46.4), 97 (42.6), 63 (100); 51(68.9). Anal. Calcd. for C18H18N5O5PS:
C 48.32, H 4.06, N 15.65. Found C 48.41, H 3.93, N 15.47.