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Volume 2003
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10.3390/M332
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Short Note

1,2-Bis(p-phenylcarbamoyl-oxy-amino-cyclohexylidene)ethane

by
Elena Scortanu
* and
Adrian A. Caraculacu
Romanian Academy, Institute of Macromolecular Chemistry "Petru Poni", Aleea Grigore Ghica Voda, Nr. 41 A, Iasi 6600, Romania
*
Author to whom correspondence should be addressed.
Molbank 2003, 2003(3), M332; https://doi.org/10.3390/M332
Submission received: 22 February 2003 / Accepted: 4 June 2003 / Published: 8 June 2003
Versions Notes
Molbank 2003 m332 i001
The experimental procedure follows the general synthesis of blocked isocyanates [1,2]. Thus, a mixture of 1,2-bis(p-isocyanato-phenyl)ethane (4,4'-dibenzyl diisocyanate) [3,4] (66 g, 0.25 mol) and cyclohexanone oxime (65 g, 0.57 mol) was dissolved in 450 mL 1,2-dichloroethane and refluxed while stirring for 2-4 h. The product of reaction precipitated with the reaction progressed. The progress of the reaction was followed by IR spectroscopy. After cooling, the solid was isolated by filtration, washed several times with acetone and dried at 100°C. The product has a white crystalline aspect (117 g, 95.51% yield).
M.p.: Between 241-250°C a mesophase was observed followed by a decomposition process (thermo-optical method).
IR (KBr, cm-1): 3350 ms (NH), 2920 ms, 2850 m (CH2), 1730 s (CONH), 1700-1680 m (sh, C=N oxime), 1580 m (NHCO, p-Ar), 1500-1490 s (p-Ar), 1410 s (Ar, CH2-N), 1320-1310 mw (CH2), 1170 s (CH2), 1130 m (C-O, C-N), 1000 s (C-O), 910 ms (C-C, skeletal), 880 m, 860 m (C-N), 830 s (p-Ar), 740 m, 700 m (C-N).
1H NMR (60 MHz δ, DMSO-d6, 70°C): 8.97 (s, NH, 2H), 7.32, 7.22, 7.08, 6.9 (m, Ar, 8H), 2.86, 2.72 (d, CH2-Ar, 4H), 2.35, 1.7, 1.25 (m, CH2, 20H).
Elemental analysis: Calculated for: C28H34N4O4: C%= 68.55; H%= 6.99; N%= 11.42. Found: C%= 68.04; H%= 7.05; N%= 11.53.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Savostianoff, E. Inf. Chem. 1981, 119-126, 216-217, 1312.
  2. Kovalenko, L. G.; et al. Plast. Massy 1986, 11, 34.
  3. Caraculacu, A. A.; et al. Rom. Pat. 81,947, 1983.
  4. Caraculacu, A. A.; Caraculacu, G. J. Macromol. Sci. Chem. 1985, A22. 631.

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MDPI and ACS Style

Scortanu, E.; Caraculacu, A.A. 1,2-Bis(p-phenylcarbamoyl-oxy-amino-cyclohexylidene)ethane. Molbank 2003, 2003, M332. https://doi.org/10.3390/M332

AMA Style

Scortanu E, Caraculacu AA. 1,2-Bis(p-phenylcarbamoyl-oxy-amino-cyclohexylidene)ethane. Molbank. 2003; 2003(3):M332. https://doi.org/10.3390/M332

Chicago/Turabian Style

Scortanu, Elena, and Adrian A. Caraculacu. 2003. "1,2-Bis(p-phenylcarbamoyl-oxy-amino-cyclohexylidene)ethane" Molbank 2003, no. 3: M332. https://doi.org/10.3390/M332

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