122
Y. M. Elkholy
Synthesis of N-thienylmaleimide Derivatives (17a--c)
A solution of 16a–c (0.01 mol) in acetic anhydride (30 ml) was heated
under reflux for 2 h. The reaction mixture was treated with ice and
water; the solid product formed on standing was collected by filtration
and recrystallized from absolute ethanol.
Compound 17a was obtained as yellow crystals (50%) from EtOH;
1
m.p. 280 C; IR: 1680 (CO) cm 1. H NMR: 1.7 (s, 3H, CH3), 6.4, 6.8
(2d, 2H, 2CH), 7.1–8.2 (m, 4H, aromatic protons). Anal. requires for
C16H10N2O2S2 (326.35): C, 58.88; H, 3.08; N, 8.58; S, 19.64. Found: C,
58.6; H, 3.2; N, 8.4; S, 19.7.
Compound 17b was obtained as yellow crystals (48%) from EtOH;
m.p. 250 C; IR: 3400–3100 (NH2), 2210 (CN), 1680 (CO) cm 1. 1H NMR:
6.4, 6.8 (2d, 2H, 2CH), 7.1–8.1 (m, 6H, aromatic-protons, and NH2).
Anal. requires for C16H8N4O2S2 (352.35): C, 54.53; H, 2.28; N, 15.89; S,
18.19. Found: C, 54.4; H, 2.6; N, 15.6; S, 18.4.
Compound 17c was obtained as yellow crystals (45%) from EtOH;
m.p. 220 C; IR: 3400–3100 (NH2), 1675 (CO), 1735 (CO) cm 1. 1H NMR:
1.3 (t, 3H, CH3); 4.2 (q, 2H, CH2); 7.1–8.1 (m, 6H, aromatic protons,
and NH2). Anal. requires for C18H13N3O4S2 (399.37): C, 54.13; H, 3.27;
N, 10.51; S, 16.05. Found: C, 54.4; H, 3.4; N, 10.4; S, 16.4
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