1,2-Ethylene-bis(o-N2-phenylene-N1,N1-dimethylformamidine)

Sergiu Coseri; Adrian A. Caraculacu

doi:10.3390/M166

and

Institute of Macromolecular Chemistry "P.Poni", Gr. Ghica Voda Alley, 41 A, 6600, Iasi, Romania

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Molecules2000, 5(7), M166;https://doi.org/10.3390/M166

This article belongs to the Section Molbank Section of Molecules, 1997-2001

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A mixture of 3.71 mmol (0.98 g) of bibenzil-2,2-di-yl-diisocyanate (1) [1] and 74.16mmol (5.42 g) of redistilled N,N-dimethylformamide (2) was refluxed under stirring for 8 h, with complete absorption of any carbon dioxide in aqueous potassium hydroxide solution [2]. The major portion of the unchanged 2 was removed by vacuum distillation. After cooling the residue is triturated with diethyl ether, and the precipitated solid is recrystallized from ethanol to afford 0.7417 g (62 %) of 3.

M.p.: 222-224°C.

IR (cm^-1): 1640; 1590 (C=N); 1510; 1480; 1370 (C-N); 840.

¹H NMR (CDCl₃): 7.63 (s, 2H, -CH=N); 7.125 (d, 4H, H_Ar); 6.87 (d, 4H, H_Ar); 3.12 (s, 12 H, -CH₃); 2.95 (s, 4H, >CH₂).

Anal. calc. for C₂₀H₂₆N₄ (322.457): C 74.50, H 8.13, N 17.37; Found: C 74.28, H 8.13, N 17.52.

References

Caraculacu, A.A.; Caraculacu, G. J. Macromol. Sci. Chem. 1985, A22(5-7), 631.
Weiner, M.L. J. Org. Chem. 1960, 25, 2245.

Sample Availability: Available from the authors.

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