Reaktion #63342

Reaktionsgleichung

sodium borohydride

N'-Cyano-N-[3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl]-1-methyl-2-(phenylmethylene)hydrazinecarboximidamide

hydrochloric acid

hydrogen chloride

Triethylamine

→

title compound

3-[3-[(1-Methyl-3-amino-1H-1,2,4-triazol-5-yl)amino]propoxy]benzenemethanol, hydrochloride

Lösungsmittel

tetrahydrofuran

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeevaporated to a red oil which
2. 2
   workup.DISSOLUTIONwas dissolved in ethyl acetate
3. 3
   Waschenwashed with sodium bicarbonate solution
4. 4
   Sonstigeevaporated
5. 5
   Sonstigeto leave an oil

Vorschrift

N'-Cyano-N-[3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl]-1-methyl-2-(phenylmethylene)hydrazinecarboximidamide (18.2 g) in tetrahydrofuran (150 ml) was treated with 5N hydrochloric acid (30 ml) at 30° C. for 30 mins. Triethylamine (20 ml) was added followed by sodium borohydride (8.0 g). The resulting mixture was stirred at room temperature for 14 hrs, diluted with ethyl acetate (150 ml) and evaporated to a red oil which was dissolved in ethyl acetate, washed with sodium bicarbonate solution and evaporated to leave an oil. This oil was treated with etheral hydrogen chloride to give the title compound as a white solid (8 g). m.p. 148°-9°. TLC silica, ethyl acetate, water, isopropanol 0.88 ammonia (25:8:15:2) Rf 0.56.

Quelle