Hydrochloric Acid → 1-[4-(2H-Tetrazol-5-yl)phenyl]ethan-1-one

Ex-78A: A suspension of 4-acetylbenznitrile (2.9 g, 20.0 mmol), sodium azide (1.43 g, 22.0 mmol) and zinc bromide (4.5 g, 20.0 mmol) in water (50 mL) was refluxed for one day. Additional water (40 mL), HCl (3M, 30 mL) and EtOAc (200 mL) were added subsequently. The mixture was stirred until no solid in the aqueous layer. The mixture was then portioned. The aqueous solution was further extracted with EtOAc (3×60 mL). The combined EtOAc was concentrated. The residue was treated with NaOH (0.25 M, 200 mL). After stirred for 50 min, insoluble material was filtered, washed with NaOH (1M). The filtrate was then acidified with HCl (conc.) to pH 3. The resulting white precipitate was filtered, washed with water and dried in vacuo to obtain 1-[4-(2H-tetrazol-5-yl)-phenyl]-ethanone as white solid. 1H NMR (DMSO-d6) δ 8.17–8.10 (m, 4H), 2.61 (s, 3H). MS m/z=188 (M+).

1. temperaturewas refluxed for one day
2. extractionThe aqueous solution was further extracted with EtOAc (3×60 mL)
3. concentrationThe combined EtOAc was concentrated
4. additionThe residue was treated with NaOH (0.25 M, 200 mL)
5. stirringAfter stirred for 50 min
6. filtrationinsoluble material was filtered
7. washwashed with NaOH (1M)
8. filtrationThe resulting white precipitate was filtered
9. washwashed with water
10. customdried in vacuo

ORD-Eintrag

ord-228157ee07eb44e19dc9905a42bbafbc

Quelldatensatz

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07094801B2