Réaction #63342

Équation de réaction

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

Solvants

tetrahydrofuran

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Autreevaporated to a red oil which
2. 2
   workup.DISSOLUTIONwas dissolved in ethyl acetate
3. 3
   Lavagewashed with sodium bicarbonate solution
4. 4
   Autreevaporated
5. 5
   Autreto leave an oil

Mode opératoire

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.

Source