Related Products of 87-13-8, These common heterocyclic compound, 87-13-8, name is Diethyl 2-(ethoxymethylene)malonate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Aniline (2.733 mL, 29.99 mMol) was stirred in diethyl ethoxymethylenemalonate (6.063 mL, 30.00 mMol) at 120-130C for 16.5 hours. T.l.c. analysis (ethyl acetate cyclohexane, 1 : 1) showed the presence of one UV-active product (Rf 0.84) and complete consumption of both starting materials. Upon cooling down of the reactionsolution to room temperature, intermediate diethyl 2-((phenylamino)methylene)malonate 35 solidified (as dark yellow crystalline solid,7.899 g, quant.). M.p. 36-37C; HRMS (EIj: found 263.11531 [M] C14H17N04requires 263.11521; Vmax (thin film): 3265, 3184 (w, NH), 3050 (w, ArC-H), 2981,2936, 2904, 2871 (m, alkyl C-H), 1717 (s, 2 x intramolecularly hydrogen-bondedC=O conjugated with C=C), 1691 (s, C=C-NH), 1655 (s, C=N-), 1623 (s, aryl conjugated C=C), 1255 (s, C-N stretch) cm?; 6H (CD3CN, 500 MHz): 1.31 (3H, t, JCH3,CH2 7.1 Hz, CH3), 1.32 (3H, t, JCH3,CH2 7.2 Hz, CH3), 4.19 (2H, q, JCH2,CH3 7.2 Hz, CH2), 4.25 (2H, q, JCH2,CH3 7.1 Hz, CH2), 7.16 (1H, tt, JparaArH,metaArHs 7.4 Hz, JparaArH,orthoArHs 1.1 Hz, para-ArH), 7.20 (2H, dt, Jortho&-Hs,metaArHs 7.6 Hz,JorthoArHsparaArH 1.0 Hz, 2 x orthoArHs), 7.38 (2H, m, J 7.4 Hz, 2 x metaArHs), 8.48(1H, d, JCH,NH 13.8 Hz, CH-NH), 10.81 (1H, d, JNH,CH 13.6 Hz, CH-NI]); 6c(CD3CN, 125 MHz): 14.1, 14.2 (2 x CH3), 60.3, 60.6(2 x CH2), 93.9 (O=C-C-C=O),117.6(2 x orthoArCs), 125.1 (paraArC), 130.1 (2 x metaArCs), 139.8 (ArCquat-NH),151.9 (NH-CH), 165.6 (C=O), 168.8 (hydrogen bonded C=O).
Statistics shows that Diethyl 2-(ethoxymethylene)malonate is playing an increasingly important role. we look forward to future research findings about 87-13-8.
Reference:
Patent; UCL BUSINESS PLC; SELWOOD, David; HOBBS, Adrian; WO2015/189560; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics