Imidazole → 1-(3-chloropropyl)-1H-imidazole

Anhydrous THF (25 mL) was cooled in an ice bath. After NaH (1.40 g, 35 mmol, 60%) was added to the THF in one portion, the mixture was stirred at rt for 30 min and cooled in an ice bath. Then a solution of 1H-imidazole (2.00 g, 30 mmol) in anhydrous THF (6 mL) was added dropwise. The reaction mixture was then warmed to rt and stirred at rt for 1.5 h. To the mixture was added 1-bromo-3-chloropropane (4.60 g, 30 mmol) dropwise, and stirred at rt overnight. To the resulting mixture was added MeOH (5 mL) in one portion. The resulting mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=30:1) to give the title compound as pale yellow oil (3.10 g, 73%).

1. temperaturecooled in an ice bath
2. temperatureThe reaction mixture was then warmed to rt
3. stirringstirred at rt for 1.5 h
4. stirringstirred at rt overnight
5. filtrationThe resulting mixture was filtered
6. concentrationthe filtrate was concentrated in vacuo
7. customThe residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=30:1)

ORD record

ord-233068654a734af28411419edc2c0521

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434695B2