Triethylamine → (E)-N-(2-azidoethyl)-2-methyl-3-phenylacrylamide

To a 25 mL round-bottomed flask equipped with a magnetic stir bar was added (E)-2-methyl-3-phenylacrylic acid (0.0.512 g, 3.15 mmol) and dichloromethane (10 mL). Oxalyl chloride (0.400 g, 3.15 mmol) was added dropwise to the reaction mixture and allowed to stir for one hour. Then, the reaction mixture was concentrated de vacuo. To the crude mixture was then added dichloromethane (10 mL), 2-azidoethanamine (0.299 g, 3.47 mmol) and then triethylamine (0.351 g, 3.47 mmol) and allowed to stir for two hours. The reaction mixture was then concentrated de vacuo and then purified via silica gel column chromatography (100% dichloromethane to 1:40 methanol:dichloromethane) to give (E)-N-(2-azidoethyl)-2-methyl-3-phenylacrylamide (0.698 g, 96% yield). 1H NMR (300 MHz, CDCl3) δ 7.39 (m, 6H), δ 7.01 (s, 1H), δ 3.51 (t, 2H), δ 3.45 (t, 2H), δ 2.13 (s, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 170.5, 136.2, 134.5, 132.0, 130.3, 129.6, 128.9, 128.6, 128.3, 50.9, 39.8, 14.5 ppm; HRMS (ESI) calcd for C12H14N4O (M+) 230.1168. Found 230.1165.

1. customTo a 25 mL round-bottomed flask equipped with a magnetic stir bar
2. concentrationThen, the reaction mixture was concentrated de vacuo
3. stirringto stir for two hours
4. concentrationThe reaction mixture was then concentrated de vacuo
5. custompurified via silica gel column chromatography (100% dichloromethane to 1:40 methanol:dichloromethane)

ORD record

ord-737c98788f874d9fb17a2bbab3bfdf56

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09145395B2