Methyl iodide → HCID 86638784, compound

Participants

Reaction Steps

In a 100 mL round bottom flask equipped with a stirbar and covered with foil, 4-[2-(4-azido-phenyl)-vinyl]-pyridine (0.57 g, 2.56 mmol) was mixed with iodomethane (0.95 g, 6.7 mmol) in acetonitrile (20 mL) and stirred at room temperature for 36 hrs. A precipitate had formed and TLC showed a single spot, so the solution was placed in the refrigerator for 30 minutes and then filtered, rinsing with diethyl ether. The product was collected as a yellow powder (0.482 g). Diethyl ether was added to the filtrates and then placed in the refrigerator for 2 hrs. Orange/brown crystals formed which were collected by suction filtration (0.15 g). The total amount of product collected was 0.63 g (68% yield). mp 166.2-168.0° C. 1H NMR (400 MHz, DMSO-d6) δ 8.86 (d, J=6.9 Hz, 2H), 8.20 (d, J=6.9 Hz, 2H), 8.01 (d, J=16.4 Hz, 1H), 7.80 (ddd, J=1.8, 2.6, 8.5 Hz, 2H), 7.49 (d, J=16.4 Hz, 1H), 7.26 (ddd, J=1.8, 2.6, 8.5 Hz, 2H), 4.26 (s, 3H). 13C NMR (100 MHz, DMSO-d6) 152.89, 145.56, 141.80, 140.08, 132.54, 130.31, 123.90, 123.28, 120.37, 47.39. λmaxCH3CN 373 nm (ε 4.07×104). IR νmax(cm−1) 2118 (N3).

Provenance & Evidence