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, J=4.5 Hz, 2H), δ 3.45 (t, J=4.8 Hz, 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-71e29d454817473ea68f697d4ec25209

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09351491B2