Diethyl Ether → HCID 15168439, compound

Participants

Reaction Steps

3,5-Dichloroaniline (104 g) and dimethylacetylene dicarboxylate (79 ml) were dissolved in dry methanol (100 ml) and heated under reflux for 14 h. On cooling a yellow solid crystallised out and this was collected by filtration. The mother liquors were concentrated in vacuo to leave a residue from which a second crop of product was obtained by recrystallisation from diethyl ether/60-80 petrol. The combined crops of material weighed 167.5 g (after drying at 40° C. under a pressure of 20 mmHg for 18 h). A portion of this material (105 g) was dissolved in ethyl acetate (1000 ml) and hydrogenated at 50 psi over 10% palladium on carbon catalyst (4 g) for 40 h. The catalyst was removed by filtration and the solvent evaporated under vacuum to leave a residue which was recrystallised from diethyl ether/hexane to give the title compound as a white crystalline solid (84.8 g, m.p. 66°-67° C.); δ (360 MHz, CDCl3 ) 2.88 (2H, m, CHBHC), 3.71 (3H, s, CH3), 3.78 (3H, s, CH3), 4.36 (1H, t, J=5.4 Hz, CHACHBHC), 4.71 (1H, br, s, NH), 6.51 (2H, d, J=1.8 Hz, 2-H and 6-H), 6.73 (1H, t, J=1.8 Hz, 4-H); m/e 305 (M+), 246 (100%, M-CO2CH2); Found C, 47.14; H, 4.27; N, 4.56. C12H13Cl2NO4 requires C, 47.08; H, 4.28; N, 4.58%.

Provenance & Evidence