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Short Note

3,5-Bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]nitrobenzene

by
Frank Osterod
and
Arno Kraft
*
Department of Organic Chemistry and Macromolecular Chemistry II, University of Düsseldorf, Universitätsstr. 1, D-40225 Düsseldorf, Germany
*
Author to whom correspondence should be addressed.
Molecules 1999, 4(10), M114; https://doi.org/10.3390/M114
Submission received: 15 September 1999 / Accepted: 15 September 1999 / Published: 8 October 1999
Versions Notes
Molecules 04 m114 i001
A solution of 5-nitroisophthaloyl dichloride (1) [1] (3.92 g, 15.8 mmol) and 4-tert-butylbenzhydrazide (2) [2] (6.08 g, 31.6 mmol) in CHCl3 (70 mL) was heated to reflux for 12 h. The solvent was then removed in vacuum, the residue was dried and combined with freshly distilled POCl3 (20 mL). The solution was heated to reflux for 3 h until evolution of HCl ceased. The resulting yellow solution was added dropwise to water (300 mL) under vigorous stirring. The precipitate was collected by suction filtration, air-dried, extracted with hot ethanol (200 mL), and dried to afford 3 as a colourless solid (3.11 g, 38%). The yield was not optimised. The extraction with ethanol was responsible for considerable losses in product and should better be replaced by a different method of purification.
Mp. : 288-290°C.
IR (KBr): 2964m; 1615m; 1535s; 1494s; 1349m; 1112m; 884m; 783m; 748m; 717m.
1H NMR (CDCl3, 500 MHz): 9.22 (t, J = 1.5 Hz, 1 H, C6H3); 9.12 (t, J = 1.5 Hz, 2 H, C6H3); 8.14 (AA'XX', 4 H, C6H4); 7.61 (AA'XX', 4 H, C6H4); 1.4 (s, 18 H, CH3).
13C NMR (CDCl3, 125 MHz): 165.9; 161.7; 156.3; 149.2; 129.7; 127.1; 127; 126.3; 123.7; 120.2; 35.2; 31.1.
EI-MS (70 eV): 524 (59, M+); 161 (92); 136 (57); 77 (100).
Anal. calc. for C30H29N5O4 (523.59): C 68.68, H 5.76, N 13.34; found: C 68.59, H 5.65, N 13.26.

Supplementary materials

Supplementary File 1Supplementary File 2

References

  1. Jennings, K. F. J. Chem. Soc. 1957, 1172.
  2. Yale, H. L.; Losee, K.; Martins, J.; Holsing, M.; Perry, F. M.; Bernstein, J. J. Am. Chem. Soc. 1953, 75, 1933. [CrossRef]
  • Sample Availability: available from the authors and from MDPI.

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MDPI and ACS Style

Osterod, F.; Kraft, A. 3,5-Bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]nitrobenzene. Molecules 1999, 4, M114. https://doi.org/10.3390/M114

AMA Style

Osterod F, Kraft A. 3,5-Bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]nitrobenzene. Molecules. 1999; 4(10):M114. https://doi.org/10.3390/M114

Chicago/Turabian Style

Osterod, Frank, and Arno Kraft. 1999. "3,5-Bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]nitrobenzene" Molecules 4, no. 10: M114. https://doi.org/10.3390/M114

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