1268
S. H. SHELKE ET AL.
1-((2-(4-Chlorobenzyl)-4-methylthiazol-5-yl)methyleneamino)-2-ethylisothiou
◦
rea (5d): Yellow solid, mp 137–139 C; IR: 3388, 3239, 3137, 3092, 2965, 1592, 1517,
1437, 1311, 1089, 985, 820, 704 cm−1; 1H NMR (CDCl3, 300 MHz): 1.32 (t, J = 6.6 Hz,
3H), 2.57 (s, 3H), 3.10 (q, J = 6.6 Hz, 2H), 4.20 (s, 2H), 5.55 (bs, 2H), 7.12 (d, J = 7.5 Hz,
2H), 7.43 (d, J = 7.5 Hz, 2H), 8.55 (s, 1H); 13C NMR (CDCl3, 75 MHz): 13.4, 16.6, 32.1,
41.0, 121.8, 128.5, 130.2, 131.5, 134.5, 145.3, 155.0, 162.2, 167.8; MF: C15H17ClN4S2;
HRMS: 353.0661 (M+H)+.
1-((4-Methyl-2-phenylthiazol-5-yl)methyleneamino)-2-propylisothiourea (5e):
Yellow solid, mp 136–138 ◦C; IR: 3393, 3236, 3140, 3094, 2968, 1593, 1516, 1431, 1313,
1282, 1226, 991, 920, 820, 758 cm−1; 1H NMR (CDCl3, 300 MHz): 1.04 (t, J = 7.2 Hz,
3H), 1.75 (m, 2H), 2.57 (s, 3H), 3.08 (t, J = 7.6 Hz,2H), 5.59 (bs, 2H), 7.42–7.44 (m,
3H), 7.92–8.01 (m, 2H), 8.55 (s, 1H); 13C NMR (CDCl3, 75 MHz): 13.4, 15.8, 22.9, 32.2,
121.5, 126.6, 129.0, 130.4, 133.3, 145.8, 155.3, 161.9, 167.8. MF: C15H18N4S2; HRMS:
319.1065 (M+H)+.
1-((2-(3-Chlorophenyl)-4-methylthiazol-5-yl)methyleneamino)-2-propylisothio
urea (5f): Yellow solid, mp 126–128 ◦C; IR: 3398, 3232, 3132, 3093, 1593, 1518, 1448,
1
1315, 1255, 1103, 999, 935, 781, 680 cm−1; H NMR (CDCl3, 300 MHz): 1.04 (t, J =
7.2 Hz, 3H), 1.75 (m, 2H), 2.57 (s, 3H), 3.07 (t, J = 7.5 Hz, 2H), 5.51 (bs,1H), 7.32–7.40
(m, 2H), 7.75–7.83 (m, 1H), 7.95 (s, 1H), 8.51 (s, 1H); 13C NMR (CDCl3, 75 MHz):
13.4, 15.8, 22.9, 32.0, 124.6, 126.5, 129.7, 129.9, 130.2, 135.0, 141.1, 145.4, 155.5, 162.1,
167.8; MF: C15H17ClN4S2; HRMS: 353.0662 (M+H) +.
1-((2-(4-Chlorophenyl)-4-methylthiazol-5-yl)methyleneamino)-2-propylisothio
urea (5g): Yellow solid, mp. 149–150 ◦C; IR: 3389, 3238, 3138, 3093, 2966, 1591, 1519,
1437, 1313, 1091, 987, 827, 704 cm−1; 1H NMR (CDCl3, 300 MHz): 1.04 (t, J = 6.9 Hz,
3H), 1.80 (m, 2H), 2.57 (s, 3H), 3.08 (t, J = 7.6 Hz, 2H), 5.53 (bs, 2H), 7.35 (d, J = 7.2 Hz,
2H), 7.90 (d, J = 7.2 Hz, 2H), 8.54 (s, 1H); 13C NMR (CDCl3, 75 MHz): 13.3, 15.7, 22.8,
32.0, 121.7, 128.7, 129.4, 131.8, 135.2, 145.5, 155.1, 161.9, 168.0; MF: C15H17ClN4S2;
HRMS: 353.0661 (M+H) +.
1-((2-(4-Chlorobenzyl)-4-methylthiazol-5-yl)methyleneamino)-2-propylisothiou
◦
rea (5h): Yellow solid, mp 118–120 C; IR: 3388, 3239, 3137, 3092, 2965, 1592, 1517,
1437, 1311, 1089, 985, 820, 704 cm−1; 1H NMR (CDCl3, 300 MHz): 1.04 (t, J = 7.2 Hz,
3H), 1.82 (m, 2H), 2.56 (s, 3H), 3.08 (t, J = 7.5 Hz, 2H), 4.21 (s, 2H), 5.54 (bs, 2H), 7.13
(d, J = 7.5 Hz, 2H), 7.44 (d, J = 7.5 Hz, 2H), 8.55 (s, 1H); 13C NMR (CDCl3, 75 MHz):
13.3, 15.7, 22.8, 32.0, 41.1, 122.1, 128.3, 129.6, 131.5, 134.5, 145.5, 155.0, 162.1, 167.8;
MF: C16H19ClN4S2; HRMS: 367.0823 (M+H)+.
1-((4-Methyl-2-phenylthiazol-5-yl)methyleneamino)-2-isopropylisothiourea
(5i): Yellow solid, mp 208–201 ◦C; IR: 3398, 3232, 3132, 3093, 1593, 1518, 1448, 1315,
1
1255, 1103, 999, 781, 680 cm−1; H NMR (CDCl3, 300 MHz): 1.40 (d, J = 6 Hz, 6H),
2.58 (s, 3H), 3.07 (t, J = 6.1 Hz, 1H), 5.51(bs,1H), 7.40–7.45 (m, 3H), 7.90–8.00 (m,
2H), 8.55 (s, 1H); 13C NMR (CDCl3, 75 MHz):13.8, 24.6, 24.7, 32.5, 121.5, 127.6, 129.0,
129.6, 133.3, 145.8, 155.3, 162.3, 169.0; MF: C15H18N4S2; HRMS: 319.1067 (M+H).
1-((2-(3-Chlorophenyl)-4-methylthiazol-5-yl)methyleneamino)-2-isopropylisoth
iourea (5j): Yellow solid, mp 120–122 ◦C; IR: 3398, 3232, 3132, 3093, 1593, 1518, 1448,
1315, 1255, 1103, 999, 781, 680 cm−1; 1H NMR (CDCl3, 300 MHz): 1.41 (d, J = 6 Hz,
6H), 2.58 (s, 3H), 3.08 (t, J = 6 Hz, 1H), 5.56 (bs,1H), 7.33–7.44 (m, 2H), 7.76–7.85
(m, 1H), 7.94 (s, 1H), 8.50 (s, 1H); 13C NMR (CDCl3, 75 MHz): 13.7, 24.6, 24.7, 32.4,
121.7, 126.0, 127.5, 129.7, 129.4, 130.9, 135.3, 140.7, 145.3, 155.4, 162.0, 168.8; MF:
C15H17ClN4S2; HRMS: 353.0679 (M+H)+.