M. H. Sherif
139 (34.80), 138 (12.40), 133 (12.40), 132 (16.90), 131 (13.50), 118 (21.30), 117
(33.70), 116 (12.40), 115 (20.20), 110 (14.60), 102 (18.00), 101 (13.50), 100
(19.50), 97 (11.20), 96 (21.30), 91 (14.60), 90 (12.40), 89 (16.90), 88 (16.90), 82
(32.60), 81 (12.40), 80 (31.50), 79 (16.90), 77 (7.90), 64 (11.20), 63 (38.20), 62
(9.00), 52 (9.00), 51 (16.90), 50 (13.50), Anal. Found: C, 53.66; H, 3.79; N, 10.23;
S, 7.69. C18H16N3BrOS requires: C, 53.86, H, 3.99; N, 10.47; S, 7.98.
Compound 5 as pale yellow crystals, yield 78 %, m.p. 280 °C. IR (KBr): 3,287
(NH), 1,705 (C=O), 1,631 (C=N), 1,389 (C=S), 1,205, 1,083 (C–O) cm-1. 1H-NMR
(DMSO—d6): d 3.61 (s, 2H, NCH2CO), 3.91 (s, 3H, OCH3), 73.00–8.01 (m, 3H,
Ar–H), 8.34 (s, 1H, CH=N), 10.35 (s, 1H, NH) ppm, MS: m/z (%) = 329 (M? ?2,
43.80), 328 (M? ?1, 35.00), 327 (M?, 51.30), 326 (M? -1, 28.80), 299 (5.00), 249
(7.50), 248 (8.80), 247 (7.50), 240 (10.00), 231 (7.50), 230 (2.50), 229 (6.30), 214
(16.30), 213 (25.00), 212 (21.30), 211 (10.00), 210 (16.30), 202 (7.50), 201 (10.00),
200 (17.50), 199 (27.50), 198 (22.50), 197 (15.00), 172 (11.30), 171 (8.80), 170
(17.50), 158 (13.80), 155 (12.50), 148 (8.80), 143 (11.30), 142 (21.30), 141 (35.00),
140 (38.80), 139 (100.00), 138 (61.30), 120 (15.00), 119 (85.00), 118 (28.80), 117
(10.50), 116 (17.50), 113 (16.30), 111 (35.00), 110 (15.00), 105 (21.30), 104
(18.80), 103 (17.50), 102 (16.30), 101 (10.00), 91 (22.50), 90 (22.50), 89 (35.00), 86
(10.00), 79 (12.50), 78 (12.50), 77 (21.30), 76 (30.00), 75 (30.00), 65 (20.00), 64
(22.50), 63 (27.50), 62 (21.30), 53 (22.50), 51 (30.00), 50 (36.30). Anal. Found: C,
40.21; H, 2.98; N, 12.63; S, 9.58. C11H10N3BrO2S requires: C, 40.37; H, 3.06; N,
12.84; S, 9.78.
5-(P-tolyl)-2-[(3-bromo-4-methoxybenzylidene) acetylhydrazino]-thiazole 4.
A solution of 3 and/or 5 (0.01 mol) in acetic anhydride (20 ml) was heated under
reflex for 2 h, then cooled and poured into ice-water. The solid obtained was filtered
off, washed with water, dried, and purified by recrystallization with benzene to give
4 and 6.
Compound 4 as pale yellow crystals; yield 63 %, m.p. 75 °C. IR (KBr): 1,712
1
(C=O), 1,622 (C=N), 1,605, 1,583 (C=C), 1,210, 1,072 (C–O) cm-1. H-NMR
(CDCl3): d 2.20 (s, 3H, CH3), 2.41 (s, 3H, COCH3), 3.89 (s, 3H, OCH3), 6.99–8.01
(m, 8H, Ar–H and H-thiazole), 8.32 (s, 1H, CH=N) ppm. MS: m/z (%) = 445 (M?
?2, 22.70), 444 (M? ?1, 22.70), 443 (M?, 18.20), 442 (M? -1, 18.20), 405
(12.10), 404 (15.20), 403 (65.20), 402 (40.90), 401 (43.90), 400 (60.60), 373 (9.10),
372 (9.10), 331 (18.20), 330 (16.70), 285 (10.60), 271 (13.60), 257 (13.60), 256
(15.20), 255 (13.60), 246 (34.80), 232 (36.40), 231 (25.80), 229 (18.20), 214
(16.70), 212 (12.10), 210 (33.30), 201 (15.20), 198 (12.10), 197 (9.10), 196 (10.60),
192 (21.20), 190 (100.00), 189 (6.10), 187 (16.70), 175 (15.20), 174 (21.20), 173
(18.20), 169 (15.20), 167 (15.20), 162 (18.20), 161 (18.20), 159 (16.70), 155
(15.20), 148 (53.00), 147 (16.70), 145 (21.20), 143 (16.70), 140 (21.20), 139
(42.40), 135 (18.20), 133 (15.20), 132 (16.70), 119 (21.20), 118 (45.50), 116
(15.20), 113 (10.60), 111 (10.60), 105 (13.60), 104 (12.10), 103 (13.60), 102
(18.20), 101 (16.70), 91 (31.80), 89 (25.80), 88 (34.80), 78 (10.60), 77 (33.30), 76
(28.80), 75 (33.30), 65 (12.10), 63 (30.30), 62 (27.30), 51 (22.70), 50 (28.80), Anl.
123