Methanol → 1-(3-Chloropropyl)-1H-tetrazole

To anhydrous DMF (25 mL) was added NaH (0.70 g, 17.50 mmol, 60%) in one portion in an ice bath, and the mixture was warmed to rt and stirred at rt for 30 min. Then a solution of 1H-tetrazole (1.00 g, 14.28 mmol) in anhydrous DMF (6 mL) was added dropwise to the mixture cooled in an ice bath. The reaction mixture was then warmed to rt and stirred for 1.5 h followed by dropwise addition of 1-bromo-3-chloropropane (2.35 g, 14.93 mmol) to the mixture. The reaction mixture was stirred further at rt overnight. MeOH (1 mL) was added in one portion, and the mixture was filtered. The filtrate was concentrated in vacuo to give the crude product, which was used for next step without further purification.

1. temperaturecooled in an ice bath
2. temperatureThe reaction mixture was then warmed to rt
3. stirringstirred for 1.5 h
4. stirringThe reaction mixture was stirred further at rt overnight
5. filtrationthe mixture was filtered
6. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-5c10bbc1562d4811b5e5f34a6dc1c948

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434695B2