5
4
A. AL-ETAIBI ET AL.
—
s, 1H, triazine H), 8.83 (s, 1H, CH—N), 13.95 (s, 1H,
(
133.6, 147.6, 149.9, 161.3, 166.0. Anal. Calcd for
C H N OS (246.29): C, 53.65; H, 4.09; N, 22.75; S,
13.02. Found: C, 53.95; H, 4.20; N, 22.79; S, 13.37%.
13
NH). C NMR: ꢁ 125.2, 130.9, 138.1, 139.8, 149.8,
50.8, 171.7, 172.1. Anal. Calcd for C H N O S
11 10 4
1
10 7 5 3
(277.26): C, 43.32; H, 2.54; N, 25.26; S, 11.56. Found:
C, 42.95; H, 2.69; N, 24.79; S, 12.51%.
4
5
2
1
-p-Nitrobenzylidenamino-3-methylthio-1,2,4-triazin-
(4H)-one (2b). Yellow crystals, yield 75%, m.p. 212–
ꢃ
þ
4
5
-p-Chlorobenzylidenamino-3(2H)-thioxo-1,2,4-triazin-
13 C. MS: m/z 291 (M , 72%). IR: 3436, 3116, 2363,
ꢃ
ꢁ
1 1
(4H)-one (1c). Yellow crystals, yield 90%, m.p. 188 C.
689 cm . H NMR (CDCl ): ꢁ 2.68 (s, 3H, SCH ), 8.08
3
3
þ
MS: m/z 266 (M , 20%), 268 (M þ 2, 7%). IR: 3437,
(
d, 2H, J ¼ 8.8 Hz, ArH), 8.38 (d, 2H, J ¼ 8.8 Hz, ArH)
ꢁ
1 1
220, 3077, 1690 cm . H NMR (CDCl ): ꢁ 7.02 (d, 2H,
13
3
—
—
8.40 (s, 1H, triazine H), 9.80 (s, 1H, CH N). C NMR:
3
J ¼ 8.4 Hz, ArH), 7.85 (d, 2H, J ¼ 8.4 Hz, ArH), 8.37 (s,
ꢁ
1
15.2, 124.5, 130.1, 138.2, 147.9, 150.2, 150.5, 161.3,
61.4. Anal. Calcd. for C H N O S (291.28): C, 45.36;
—
H, triazine H), 9.20 (s, 1H, CH—N), 10.66 (s, 1H, NH).
1
11 9 5 3
1
3
C NMR: ꢁ 129.3, 129.6, 130.4, 130.6, 139.7, 148.9,
70.7, 171.2. Anal. Calcd for C H N OSCl (266.7): C,
H, 3.11; N, 24.04; S, 11.01. Found: C, 45.33; H, 3.21; N,
23.96; S, 11.11%.
1
4
2
10 7 4
5.03; H, 2.65; N, 21.01; S, 12.02. Found: C, 45.13; H,
.85; N, 21.06; S, 12.00%.
4
5
1
-p-Chlorobenzylidenamino-3-methylthio-1,2,4-triazin-
(4H)-one (2c). Yellow crystals, yield 72%, m.p. 155–
4
5
-p-Methylbenzylidenamino-3(2H)-thioxo-1,2,4-triazin-
þ
ꢃ
56 C. MS: m/z 280 (M , 8%), 282 (M þ 2, 22%). IR:
ꢃ
(4H)-one (1d). Yellow crystals, yield 60%, m.p. 197 C.
ꢁ1 1
þ
3436, 1680, 1605, 1592 cm . H NMR (CDCl
(s, 3H, SCH
3
): ꢁ 2.59
), 7.44 (d, 2H, J ¼ 8.5 Hz, ArH), 7.76 (d, 2H,
MS: m/z 246 (M , 45%). IR: 3439, 3085, 3054,
ꢁ
959,1712 cm . H NMR (CDCl ): ꢁ 2.46 (s, 3H,
3
1
1
3
2
J ¼ 8.5 Hz, ArH) 8.31 (s, 1H, triazine H), 9.38 (s, 1H,
CH ), 7.32 (d, 2H, J ¼ 8.0 Hz, ArH), 7.83 (d, 2H,
13
CH—N). C NMR: ꢁ 15.1, 129.8, 130.6, 130.9, 139.8,
3
—
J ¼ 8.0 Hz, ArH), 7.69 (s,1H, triazine H), 8.43 (s, 1H,
13
147.6, 150.0, 161.2, 164.1. Anal. Calcd. for
C H N OSCl (280.73): C, 47.06; H, 3.23; N, 19.96; S,
—
CH—N), 10.87 (s, 1H, NH). C NMR: ꢁ 21.8, 128.5,
11 9 4
1
Calcd for C H N OS (246.29): C, 53.65; H, 4.09; N,
29.5, 129.7, 138.0, 144.53, 149.2, 171.5, 172.2. Anal.
11.42. Found: C, 47.03; H, 3.36; N, 19.80; S, 11.43%.
11 10 4
2
1
2.75; S, 13.02. Found: C, 53.44; H, 4.09; N, 22.70; S,
3.15%.
4
5
-p-Methylbenzylidenamino-3-methylthio-1,2,4-triazin-
ꢃ
(4H)-one (2d). Yellow crystals, yield 83%, m.p. 129 C.
þ
MS: m/z 260 (M , 80%). IR: 3354, 3057, 3015, 2928,
4
zin-5(4H)-one (1e). Yellow crystals, yield 67%, m.p.
-p-Methoxybenzylidenamino-3(2H)-thioxo-1,2,4-tria-
ꢁ
682 cm . H NMR (CDCl ): ꢁ 2.38 (s, 3H, CH ), 2.57
3 3
1 1
1
ꢃ
þ
(s, 3H, SCH ), 7.22 (d, 2H, J ¼ 8 Hz, ArH), 7.70 (d, 2H,
1
2
65–167 C. MS: m/z 262 (M , 80%). IR: 3157, 3051,
3
ꢁ1
1
971, 1712 cm . H NMR (CDCl ): ꢁ 3.92 (s, 3H,
J ¼ 8 Hz, ArH) 8.29 (s, 1H, triazine H), 9.22 (s, 1H,
3
13
—
CH—N). C NMR: ꢁ 14.8, 21.8, 129.3, 129.4, 129.8,
OCH ), 7.01 (d, 2H, J ¼ 8.8 Hz, ArH), 7.90 (d, 2H,
3
1
44.3, 147.3, 149.7, 161.0, 166.0. Anal. Calcd for
OS (260.31): C, 55.37; H, 4.65; N, 21.52; S,
2.32. Found: C, 55.76; H, 4.66; N, 21.52; S, 12.52%.
J ¼ 8.8 Hz, ArH), 7.68 (s, 1H, triazine H), 8.38 (s, 1H,
13
—
CH—N), 10.60 (s, 1H, NH). C NMR: ꢁ 55.6, 114.5,
C H N
12 12 4
1
123.9, 131.6, 137.9, 149.3, 163.9, 171.5, 171.7. Anal.
Calcd for C H N O S (262.2): C, 50.37; H, 3.84; N,
11 10 4 2
2
1
1.36; S, 12.23. Found: C, 50.63; H, 3.84; N, 21.28; S,
2.75%.
4-p-Methoxylbenzylidenamino-3-methylthio-1,2,4-tria-
zin-5(4H)-one (2e). White crystals, yield 65%, m.p.
ꢃ
þ
68 C. MS: m/z 276 (M ). IR: 3440, 3056, 3011,
2932, 1683 cm . H NMR (CDCl ): ꢁ 2.57 (s, 3H,
1
ꢁ
1
1
Preparation of 4-arylidenamino-3-methylthio-1,
,4-triazin-5(4H)- ones (2a–e). A mixture of each of
a–e (10 mmol) and methyl iodide (10 mmol) in DMF
5 ml) and triethylamine (10 mmol) was stirred at room
3
2
1
(
SCH ), 3.84 (s, 3H, OCH ), 6.95 (d, 2H, J ¼ 8.8 Hz,
3
3
ArH), 7.78 (d, 2H, J ¼ 8.8 Hz, ArH), 8.30 (s, 1H, triazine
—
13
H), 9.12 (s, 1H, CH—N). C NMR: ꢁ 14.8, 55.5, 114.5
124.4, 131.3, 147.1, 149.6, 160.8, 163.8, 165.7. Anal.
Calcd. for C H N O S (276.31): C, 52.16; H, 4.38; N,
temperature overnight. After dilution with water, the
precipitate was collected, washed with water several
times and recrystallized from ethanol to give crystals of
compounds 2a–e.
12 12 4 2
20.28; S, 11.60. Found: C, 52.35; H, 4.33; N, 20.41; S,
12.09%.
4
-Benzylidenamino-3-methylthio-1,2,4-triazin-5(4H)-one
ꢃ
(2a). Yellow crystals, yield 75%, m.p. 111–112 C. MS:
Acknowledgements
þ
ꢁ1 1
m/z 246 (M , 45%). IR: 3157, 3051, 2971, 1712 cm . H
NMR (CDCl ): ꢁ 2.58 (s, 3H, SCH ), 7.46 (t, 2H,
The support of the University of Kuwait received through
research grant (SC03/00) and the facilities of Analab/
SAF (GS01/01, GS02/01, GS03/01) is gratefully ac-
knowledged.
3
3
J ¼ 7.6 Hz, ArH), 7.54 (t, 1H, J ¼ 7.6 Hz, ArH), 7.83 (d,
2
H, J ¼ 7.6 Hz, ArH), 8.31 (s, 1H, triazine H), 9.33 (s,
—
13
1
H, CH—N). C NMR: ꢁ 15.1, 129.3, 129.5, 132.3,
Copyright # 2003 John Wiley & Sons, Ltd.
J. Phys. Org. Chem. 2004; 17: 49–55