Molecules 2019, 24, 1175
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1
eq) (viz; phenyl isocyanate, p-chloro-, m-methyl- and m-methoxyphenyl isocyanate) to a hot solution
of IV, XIII or XXII (1.2 mmol) in dry toluene (5 mL). The mixture was refluxed for 3–5 h till precipitation
occurs. The precipitate was filtered while hot, washed with toluene and crystallized from EtOH to
afford the title compounds [31].
3
.2.20. 1-(4-((3-Methylquinoxalin-2-yl)amino)phenyl)-3-phenylthiourea (VIIIa)
◦
1
Olive green solid (yield = 76%); m.p. 175–176 C; H-NMR (DMSO-d )
δ: 10.36 (s, 1H, NH
6
thiourea), 10.03 (s, 1H, NH thiourea), 8.90 (s, 1H, NH), 8.00–6.82 (m, 13H, Ar-H), 2.70 (s, 3H, CH );
3
−
1
FT-IR (
(
ύ
max, cm ): 3354 (3 NH), 3053 (CH aromatic), 2950 (CH aliphatic), 1219 (C=S amide); MS
MWt: 385.5): m/z, 385 [M , (1%)], 93.05 (100%); Anal. calcd for C H N S: C, 68.55; H, 4.97; N, 18.17.
+
22
19
5
Found: C, 68.69; H, 5.03; N, 18.42.
3
.2.21. 1-(4-((3-Methylquinoxalin-2-yl)amino)phenyl)-3-phenylurea (VIIIb)
◦
1
Brown solid (yield = 68%); m.p. > 300 C; H-NMR (DMSO-d ) δ: 9.78 (s, 1H, NH urea), 9.68 (s,
6
−
1
1
H, NH urea), 8.65 (s, 1H, NH), 7.95–7.11 (m, 13H, Ar-H), 2.72 (s, 3H, CH ); FT-IR (
ύ
max, cm ): 3356
3
(
[
3 NH), 3055 (CH aromatic), 2993 (CH aliphatic), 1640 (C=O amide); MS (MWt.: 369.42): m/z, 370.28
M + H, (5.17)],369.29 [M , (7.41%) ], 40.36 (100%); Anal. calcd for C H N O: C, 71.53; H, 5.18; N,
22 19 5
+
+
1
8.96. Found: C, 71.80; H, 5.26; N, 19.18.
.2.22. 1-(4-Chlorophenyl)-3-(4-((3-methylquinoxalin-2-yl)amino)phenyl)urea (VIIIc)
3
8
◦
1
Greyish-brown solid (yield = 79%); m.p. 248–249 C; H-NMR (DMSO-d )
δ: 8.85 (s, 1H, NH urea),
6
.65 (s, 1H, NH urea), 8.57 (s, 1H, NH), 7.86 (d, J = 8 Hz, 2H, Ar-H), 7.79 (d, J = 8 Hz, 1H, Ar-H), 7.64 (d,
J = 8 Hz, 1H, Ar-H), 7.56 (t, 1H, Ar-H), 7.53 (d, J = 3.2 Hz, 2H, Ar-H), 7.49 (d, J = 8 Hz, 2H, Ar-H), 7.43
t, 1H, Ar-H), 7.34 (d, J = 8 Hz, 2H, Ar-H), 2.70 (s, 3H, CH3); 1 C-NMR (DMSO-d6)
3
δ: 154.00, 149.00,
(
1
1
4
47.50, 139.00, 138.80, 137.00, 135.00, 129.50, 129.00, 128.00, 127.50, 127.00, 126.00, 125.00, 123.00, 120.00,
−
1
17.70, 22.00; FT-IR (
03.86): m/z, 405.04 [M + 2,(1.28%) ], 403.89 [M , (0.9%)], 89.99 (100%); Anal. calcd for C H ClN O:
ύ max, cm ): 3464 (3 NH), 3059 (CH aromatic), 1635 (C=O amide); MS (MWt.:
+
+
22
18
5
C, 65.43; H, 4.49; N, 17.3. Found: C, 65.58; H, 4.57; N, 17.51.
3
.2.23. 1-(4-((3-Methylquinoxalin-2-yl)amino)phenyl)-3-(m-tolyl)urea (VIIId)
◦
1
Black solid (yield = 65%); m.p. 280–281 C; H-NMR (DMSO-d )
δ
: 9.18 (s, 1H, NH urea), 8.57
s, 1H, NH urea), 8.56 (s, 1H, NH), 7.85 (d, J = 8 Hz, 1H, Ar-H), 7.71–7.46 (m, 4H, Ar-H), 7.35 (s, 1H,
Ar-H), 7.31 (m, 1H, Ar-H), 7.23 (d, J = 8 Hz, 2H, Ar-H), 7.14 (t, 1H, Ar-H), 6.78 (d, J = 8 Hz, 2H, Ar-H),
6
(
−
.49 (s, 3H, CH ), 2.27 (s, 3H, CH ); FT-IR (ύ max, cm ): 3456 (3 NH), 3035 (CH aromatic), 2958 (CH
3 3
aliphatic), 1639 (C=O amide); MS (MWt: 383.45): m/z, 384.12 [M + H, (3.19%)], 383.12 [M , (12.44%)],
1
2
+
+
2
49.08 (100%); Anal. calcd for C H N O: C, 72.04; H, 5.52; N, 18.26. Found: C, 72.23; H, 5.61; N, 18.42.
23 21 5
3
.2.24. 1-(3-Methoxyphenyl)-3-(4-((3-methylquinoxalin-2-yl)amino)phenyl)urea (VIIIe)
◦
1
Black solid (yield = 79%); m.p. 228–230 C; H-NMR (DMSO-d )
δ: 8.68 (s, 1H, NH urea), 8.60
6
(s, 1H, NH urea), 8.57 (s, 1H, NH), 7.86 (d, J = 8 Hz, 2H, Ar-H), 7.79 (d, J = 8 Hz, 1H, Ar-H), 7.64 (d,
J = 8 Hz, 1H, Ar-H),7.53 (t, 1H, Ar-H), 7.47 (d, J = 8 Hz, 2H, Ar-H), 7.42 (t, 1H, Ar-H), 7.38 (s, 1H,
Ar-H), 7.22–7.20 (m, 1H, Ar-H), 7.18 (d, J = 8 Hz, 1H, Ar-H), 6.95 (d, J = 8 Hz, 1H, Ar-H), 3.74 (s, 3H,
13
OCH ), 2.71 (s, 3H, CH ); C-NMR (DMSO-d6)
δ: 160.00, 153.00, 149.00, 146.00, 142.00, 141.00, 137.00,
3
3
1
36.00, 135.00, 130.00, 129.00, 127.00, 126.00, 125.00, 123.00, 118.00, 111.00, 109.00, 105.00, 55.00, 22.00;
−
1
FT-IR (
ύ
max, cm ): 3298 (3 NH), 3059 (CH aromatic), 2935 (CH aliphatic),1639 (C=O amide); MS
+
+
(MWt: 399.45): m/z, 400.85 [M + H, (2.88%) ], 399.24 [M , (11.49%) ], 54.07 (100%); Anal. calcd for
C H N O : C, 69.16; H, 5.30; N, 17.53. Found: C, 69.41; H, 5.37; N, 17.65.
23
21
5
2