Water → HCID 22936895, compound

A suspension of sodium hydride (1.55 g, 30.8301 mmol, 60% in oil) in hexane was allowed to stand, and after removing the supernatant, dimethylformamide (25 ml) was added thereto to forma suspension and 1H-1,2,3-triazole (1.5 ml, 25.8867 mmol) was added dropwise while cooling on ice. This was stirred at room temperature for 5 minutes to thorough dissolution, and then 1-bromo-3-chloropropane (2.82 ml, 28.4754 mmol) was added and the mixture was stirred at room temperature for 8 hours. After adding water while cooling on ice, the mixture was extracted with diethyl ether and then with ethyl acetate, washed with saturated brine and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the isomers were separated by NH silica gel column chromatography (hexane-ethyl acetate) and purified to obtain low polarity 2-(3-chloropropyl)-1,2,3-triazole (0.429 g, 2.9466 mmol, 11.38%) and high polarity 1-(3-chloropropyl)-1,2,3-triazole (0.910 g, 6.2504 mmol, 24.15%) as colorless oils.

1. customafter removing the supernatant, dimethylformamide (25 ml)
2. additionwas added
3. temperaturewhile cooling on ice
4. stirringthe mixture was stirred at room temperature for 8 hours
5. temperaturewhile cooling on ice
6. extractionthe mixture was extracted with diethyl ether
7. washwith ethyl acetate, washed with saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. distillationthe solvent was distilled off under reduced pressure
10. customthe isomers were separated by NH silica gel column chromatography (hexane-ethyl acetate)
11. custompurified

ORD record

ord-db33a9720d4541168006238b7db872c7

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07973160B2