反応 #10799

反応方程式

4-acetylbenznitrile

sodium azide

HCl

EtOAc

→

1-[4-(2H-tetrazol-5-yl)-phenyl]-ethanone

溶媒

water

water

反応条件

後処理

1. 1
   温度was refluxed for one day
2. 2
   抽出The aqueous solution was further extracted with EtOAc (3×60 mL)
3. 3
   濃縮The combined EtOAc was concentrated
4. 4
   workup.ADDITIONThe residue was treated with NaOH (0.25 M, 200 mL)
5. 5
   workup.STIRRINGAfter stirred for 50 min
6. 6
   ろ過insoluble material was filtered
7. 7
   洗浄washed with NaOH (1M)
8. 8
   ろ過The resulting white precipitate was filtered
9. 9
   洗浄washed with water
10. 10
    その他dried in vacuo

実験手順

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+).

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