1H-1,2,4-Triazole → HCID 18406943, compound

To a solution of [1,2,4]triazole (7.3 g, 0.11 mol), triphenylphosphine (33 g, 0.13 mol) and 2,2-difluoroethanol (8.0 ml, 10 g, 0.13 mol) in THF (115 ml) was added diethyl azodicarboxylate (20 ml, 22 g, 0.13 mol) dropwise, maintaining the temperature of the mixture between −5 and 0° C. throughout the addition. The resultant solution was allowed to warm to room temperature and was stirred under nitrogen overnight. The solvent was removed it uacuo, and diethyl ether (220 ml) was added to the residue, precipitating a solid. This was separated by filtration, and the filtrate was concentrated in vacuo. The residual oil was purified by distillation under vacuum, yielding 1-(2,2-difluoroethyl)-1H-[1,2,4]triazole as a yellow oil (7.1 g). Data for the title compound: 1H NMR (250 MHz, CDCl3) δ 4.56 (2H, td, J=13.5, 4.1 Hz), 6.13 (1H, tt, J=55.1, 4.2 Hz), 8.01 (1H, s), 8.18 (1H, s).

1. temperaturemaintaining the temperature of the mixture between −5 and 0° C.
2. additionthroughout the addition
3. customThe solvent was removed it uacuo
4. additiondiethyl ether (220 ml) was added to the residue
5. customprecipitating a solid
6. customThis was separated by filtration
7. concentrationthe filtrate was concentrated in vacuo
8. distillationThe residual oil was purified by distillation under vacuum

ORD record

ord-5abdd9a9e3c24734a29efb8ce2bf72f9

Source dataset

uspto-grants-2002_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06476030B1