W. Watson, Guanmin Wu, M. Richmond
Sep 1, 2004
Citations
1
Influential Citations
2
Citations
Journal
Journal of Chemical Crystallography
Abstract
The reaction of p-toluidine with 2,3-dichloromaleic anhydride in the presence of added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) does not give the known compound 2-chloro-3-p-toluidino-N-p-tolylmaleimide (1), but rather 2-p-toluidino-N-p-tolylmaleimide (2) in low yields. Repeating this same reaction with Et3N, pyridine, tmeda, and 4-Me2Npyridine in place of DBU furnishes the expected product 2-chloro-3-p-toluidino-N-p-tolylmaleimide, without the presence of 2-p-toluidino-N-p-tolylmaleimide. The participation of DBU in the chlorine for hydrogen exchange reaction in compound 1 has been demonstrated from the independent thermolysis reaction of 1 with DBU in toluene, where 2 was obtained as the sole isolable product. Compound 2 was isolated and fully characterized in solution, and the molecular structure was established by X-ray diffraction analysis. 2-p-Toluidino-N-p-tolylmaleimide crystallizes in the monoclinic space C2/c, a = 33.630(5), b = 12.508(2), c = 7.381(1), β = 90.668(3), V = 3104.3(8)3, Z = 8, and Dcalc = 1.251 Mg/m3; R = 0.0357, Rw = 0.0896 for 2011 reflections with I > 2σ(I).