4-(5-Methyl-2-furfuryl)iden-2-furfurylaminobutanolide
Lyudmila N. Sorotskaya, Tat'yana Ya. Kaklyugina and Larisa A. Badovskaya
Laboratory of Furan Chemistry, Kuban State Technological University, Moskovskaya st. 2, Krasnodar 350072, Russia, E-mail: [email protected], E-mail: [email protected]
Received: 1 February 2000 / Accepted: 7 February 2000 / Published: 23 February 2000
4-(5-Methyl-2-furfuryl)iden-2-furfurylaminobutanolide was prepared by the reaction of 4-(5-methyl-2-furfuryl)iden-2-butenolide and furfurylamine according to a literature procedure [1]. A mixture of 4-(5-methyl-2-furfuryl)iden-2-butenolide (1.76 g, 0.01 mol) and furfurylamine (2.94 g, 0.03 mol) was allowed to stand at room temperature for 24 h and then cooled to 0 °C for crystallization. The precipitate obtained was collected by filtration, washed with cold ethanol and recrystallized from ethanol to give 1.31 g (48 %) of the titled product.
M.p. 172-173 ° C (ethanol).
IR (nujol, cm-1): 3200 (NH), 1680 (C=O), 1650 (C=C).
UV [lmax(nm), log e (dm3mol-1cm-1)] (ethanol): 318 (4.48).
1H NMR (CDCl3, 250 MHz): 7.37 (dd, 1H, HK, JKJ = 1.3 Hz; JKI = 1.0 Hz); 6.32 (m, HJ, HI); 7.08 (t, HC, JCD = JCE = 2.5 Hz); 6.43 (dd, 1H, HB, JBA = 3.5 Hz); 6.06 (dd, 1H, HA, JAB = 3.52 Hz); 5.26 (ddd, 1H, HF, JFG = 9.0 Hz; JFD = 7.0 Hz; JFE = 2.0 Hz); 4.85 (d, 1H, HH, JHL = 15.5 Hz); 4.38 (d, 1H, HL, JLH = 15.5 Hz); 3.48 (d, 1H, HG, JGF = 9.0 Hz); 3.31 (ddd, 1H, HD, JDE = 19.0 Hz; JDF = 7.0 Hz; JDC = 2.5 Hz); 2.93 (ddd, 1H, HE, JED = 19.0 Hz; JEF = 2.0 Hz; JEC = 2.5 Hz); 2.33 (d, 3H, CH3).
Anal. calc. for C15H14NO4 (234,25): C 65.93, H 5.49, N 5.12. Found: C 65.60, H 5.60, N 4.98.
Reference
1. Sorotskaya L.N., Badovskaya L.A., Nen'ko N.I., Arustamova I.S. Khimiya i tekhnologiya furanovykh soedineniy (Chemistry and technology of furan compounds, Collection of scientific transactions, Russia) 1997, 126-133.
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