Sodium prop-2-enolate → 6-allyloxy-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-nitropyridine-2-amine

Participants

Reaction Conditions

Reaction Steps

1.10 g of 6-chloro-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-nitropyridine-2-amine, prepared according to the example 1, in 30 mL of DMF was added into a 100 mL three-necked flask equipped with a magnetic stirrer, a condenser and a drying tube, under stirring at 5-10° C., 1.02 g of sodium prop-2-en-1-olate (the content of 30.7%) in 20 mL of DMF was added dropwise, and the reaction was complete after further stirred for 4 to 6 hours. The reaction mixture was treated by the method according to the example 1 to obtain 0.25 g of 6-allyloxy-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-nitropyridine-2-amine, having the content of 91%, as a brown sticky solid in a yield of 19.4%. GC-MS (M+) (EI, 70 eV, m/z) calc: 354. found: 354. 1H NMR (CDCl3/TMS, 300 MHz) δ (ppm) 1.221 (t, J=7.2 Hz, 3H, CH3), 3.291 (q, J=7.2 Hz, 2H, CH2), 4.817 (s, 2H, CH2), 4.869 (d J=2.7 Hz, 2H, CH2), 5.464-5.267 (m, 2H, CH2), 6.086-5.957 (m, 1H, CH), 6.231 (d, J=8.7 Hz, 1H, Py H), 7.473 (s, 1H, Thiazole-H), 8.171 (d, J=8.7 Hz, 1H, Py H).

Provenance & Evidence