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. ES m/z: [M+H]+ calcd for C7H6N4, 147.1; found 147.1.

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-1d320bdd5545478cb9a4e533712c4892

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481549B2