DIB-b (blue) synthesis
- Product Name:DIB-b (blue)
- CAS Number:4506-61-0
- Molecular formula:C20H14N4
- Molecular Weight:310.35
Yield:4506-61-0 90%
Reaction Conditions:
in 1,2-dimethoxyethane at 190; for 4 h;
Steps:
2,20-(1,2-phenylene)bis-1H-benzimidazole, PhBIm2, (1) wassynthesized as followed:
o-Phenylenediamine (6.09 g, 56.38 mmol)and dimethyl phthalate (4.6 ml, 28.19 mmol) were stirred in ethyleneglycol (20 ml) at 190 C for 4 h. During reaction, the evolvedmethanol was distilled out. Then, the mixture was allowed tocool-down to ambient temperature and stirred overnight. The productwas treated with water (120 ml), filtered, washed with water(4 20 ml) and finally dried at 60 C under vacuum for two days togive a beige powder. Yield 7.80 g (25.16 mmol, 90%). 1H NMR(300 MHz, J = Hz, D2O/HCl, r.t.) d (ppm) = 7.46 (dd, AA¢XX¢ system,4H, JH-H = 3, HBz), 7.58 (dd, AA¢XX¢ system 4H, JH-H = 3; HBz), 7.91(dd, AA¢XX¢ system, 2H, JH-H = 3; HPh), 8.01 (dd, AA¢XX¢ system,2H, JH-H = 3 Hz; HPh). 13C {1H} NMR (75 MHz, D2O/HCl, r.t.) d(ppm) = 113.62 (CBz), 126.67 (CBz), 132.28 (CPh), 133.64 (CPh),145.79 (Cq, Bz), 130.98 (Cq, Ph PhCq), 122.24 (Cipso). IR (KBr, t/cm1), 3000 (NH, s), 3050 (Ar-H, s), 1625-1525 (ArC = C, CN,m), 1430, 1410 (NH, s), 1275 (CN, s), 750 (Ar-H, m). Anal. Calc.for C20H14N4 (F.W. 310.35) C 77.40, H 4.55, N 18.05%. Found C77.62, H 4.45, N 17.66%.
References:
Chirinos, Juan;Ibarra, Darmenia;Morillo, ángel;Llovera, Ligia;González, Teresa;Zárraga, Jeannette;Larreal, Oswaldo;Guerra, Mayamarú [Polyhedron,2021,vol. 203,art. no. 115232]
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