Benzonitrile → HCID 178418369, compound

Temperature

100 °C

A solution of benzonitrile (60.0 g, 581.9 mmol, 1.0 equiv) in DMF (anhydrous) (600 mL) was placed in a flask that had been purged and maintained with an inert atmosphere of nitrogen. Ammonium chloride (40.5 g, 757.2 mmol, 1.3 equiv) was added, followed by the addition of lithium chloride (2.0 g, 47.2 mmol, 0.1 equiv). To the mixture was added azidosodium (49.4 g, 756.8 mmol, 1.3 equiv). The resulting solution was stirred overnight, while maintaining the temperature at 100° C. The solids were filtered out and washed with EtOAc. The filtrates were combined and concentrated in vacuo. The residue was dissolved in a 10% NaOH aqueous solution (350 ml). The resulting solution was extracted with EtOAc (100 mL) and the aqueous layers were combined. The pH value of the solution was adjusted to 2 with concentrated HCl. The solids were filtered out and dried over reduced pressure to yield 5-phenyl-1H-tetrazole (78.0 g) as a white solid.

1. customthat had been purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. filtrationThe solids were filtered out
4. washwashed with EtOAc
5. concentrationconcentrated in vacuo
6. dissolutionThe residue was dissolved in a 10% NaOH aqueous solution (350 ml)
7. extractionThe resulting solution was extracted with EtOAc (100 mL)
8. filtrationThe solids were filtered out
9. customdried over reduced pressure

ORD record

ord-b097904db1b247fb8f991b160eb3c49e

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181206B2