Molecules 1999, 4, M114

Molecules 1999, 4, M114

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

Frank Osterod and Arno Kraft*

Department of Organic Chemistry and Macromolecular Chemistry II, University of Düsseldorf, Universitätsstr. 1, D-40225 Düsseldorf, Germany. Phone: +49-211-8115362, Fax: +49-211-8114788, E-mail: [email protected].

*New address: Department of Chemistry, Heriot-Watt University, Riccarton, Edinburgh EH14 4AS, United Kingdom. Phone: +44-131-4513109, Fax: +44-131-4513180, E-mail: [email protected].

Received: 15 September 1999 / Accepted: 15 September 1999 / Published: 8 October 1999

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.

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.

Sample availability: available from the authors and from MDPI.