alpha-Bromo-o-chlorotoluene → 2-Chlorobenzyl azide

A mixture of 1-(bromomethyl)-2-chlorobenzene (5 g, 24.3 mmol) and sodium azide (2.37 g, 36.5 mmol) in acetonitrile (48.7 mL) was refluxed for 3 h under N2 atmosphere. Then, the mixture was filtered and concentrated in vacuo. The residue was diluted in DCM, washed with H2O and brine, dried over Na2SO4 and concentrated in vacuo to afford crude 1-(azidomethyl)-2-chlorobenzene. The residue was used for the next reaction without further purification. A mixture of the above crude residue, 2-cyanoacetamide (1.82 g, 21.7 mmol) and sodium ethanolate (1.47 g, 21.7 mmol) in ethanol (43.3 mL) was refluxed for 3 h under N2 atmosphere. The mixture was concentrated in vacuo, diluted with 4M AcOH aq. and filtered. The residue was washed with H2O and dried in vacuo to afford 5-amino-1-(2-chlorobenzyl)-1H-1,2,3-triazole-4-carboxamide as pale-orange solid (5.10 g, 94% for 2 steps). MS(m/e): 252.1 (MH+).

1. temperaturewas refluxed for 3 h under N2 atmosphere
2. filtrationThen, the mixture was filtered
3. concentrationconcentrated in vacuo
4. additionThe residue was diluted in DCM
5. washwashed with H2O and brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo

ORD record

ord-42d473ce646e4e11bc6b9c4f0d01f47b

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056866B2