Reaktion #348984

Reaktionsgleichung

1-benzyl-2-formylimidazole

hydrazoic acid

tetrazole

sodium azide

1-benzyl-2-cyanoimidazole

ammonium chloride

→

1-Benzyl-2-(5-tetrazolyl)-imidazole

Lösungsmittel

dimethylformamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeObtained
2. 2
   Sonstigeat 120°-130° C
3. 3
   Temperaturit is cooled
4. 4
   Sonstigethe precipitate formed
5. 5
   Filtrationfiltered off
6. 6
   Sonstigerecrystallised several times from dimethylformamide

Vorschrift

Obtained by reacting 9.3 g (0.05 mol) of 1-benzyl-2-formylimidazole (see Liebigs Ann. Chem. 718 (1968) pp. 249-259) with 8.0 g (0.15 mol) of ammonium chloride and 9.8 g (0.15 mol) of sodium azide in 50 ml of dimethylformamide at 120°-130° C. The isolation of the 1-benzyl-2-cyanoimidazole intermediate (obtained by Schmidt-rearrangement) may be omitted, since this compound adds excess hydrazoic acid to the tetrazole in situ. After 20 hours, it is cooled, and 500 ml of water are added, the precipitate formed filtered off and recrystallised several times from dimethylformamide. M.p. 274°-275° C.

Quelle