2-Cinnamyl-1,3-oxazole-4-carboxaldehyde p-toluenesulfonyl hydrazone : To a stirred solution of p-toluene sulfonyl hydrazide (0

Molecules 2001, 6, M269

2-Cinnamyl-1,3-oxazole-4-carboxaldehyde p-Toluenesulfonyl Hydrazone

Fahim Ahmed

Department of Chemistry, Marquette University, P O Box 1881, Milwaukee, WI 53201-1881, USA
E-mail: [email protected]

Received: 27 October 2001 / Accepted: 15 December 2001 / Published: 20 December 2001

To a stirred solution of p-toluenesulfonhydrazide (0.61g, 3.3 mmol) in methanol/water (6:4, 20 ml) at 60°C was added 2-cinnamyl-1,3-oxazole-4-carboxaldehyde [1](0.50 g, 2.5 mmol). The solution was cooled to room temperature and stored in the refrigerator overnight. The precipitate which formed was collected by filtration and washed with methanol/water mixture (6:4, 10 mL) to give 2-cinnamyl-1,3-oxazole-4-carboxaldehyde p-toluenesulfonyl hydrazone as a colorless solid (0.66 g, 72%).

M.p. 177-179 °C.

¹H NMR (CDCl₃): 12.04 (s, 1H); 7.93-7.82 (m, 3H); 7.64-7.62 (m, 3H); 7.46-7.43 (m, 3H); 7.42-7.34 (m, 3H); 6.90 (d, J=16.7, 1H); 2.42 (s, 3H).

¹³C NMR (CDCl₃): 163.0, 144.7, 139.0, 138.9, 137.3, 136.0, 135.3, 129.9, 129.8, 129.5, 128.9, 127.8, 127.4, 114.4, 21.4.

IR (neat): n_max 3149, 2934, 2919, 1716, 1648, 1060, 962, 805cm^-1.

Anal.calc. for C₁₉H₁₇N₃O₃S (367.43): C 62.11, H 4.66, N 11.44; found: C 62.15, H 4.73, N 11.26.

Acknowledgment: The Financial support of the National Institute of Health (GM-42641) and the Marquette University Graduate School is acknowledged. The author would like to thank Dr. William A. Donaldson (E-mail: [email protected]) for his encouragement.

Reference

1. Evans, D.A.; Fitch, D. M.; Smith, T. E.; Cee, V. J. Application of Complex Aldol Reactions to the total Synthesis of Phorboxazole B. J. Am. Chem. Soc. 2000, 122, 10033-10046.

Sample Availability: Available from the author and from MDPI.