Benzaldehyde → 1-Hydroxy-3-benzylidenetriazene

Participants

Reaction Steps

To hydrazine hydrate (50 ml) was added dropwise benzaldehyde (10 ml) under ice-cooling. The mixture was stirred for 2 hours at ambient temperature. After water was added to the mixture, the resultant mixture was extracted with chloroform, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a residue, which was dissolved in dry ether. To the solution was added triethylamine (13.80 ml) and then trimethylchlorosilane (12.57 ml). The reaction mixture was stirred for 2 hours at ambient temperature. Insoluble materials were removed by filtration. The filtrate was concentrated under reduced pressure to give a residue, to which was added dichloromethane (30 ml). Nitrogen trioxide was passed through the reaction mixture for 3 hours at -20° C. The resultant mixture was poured into ice water. The organic layer was separated, washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give oily 1-hydroxy-3-benzylidenetriazene (1.7 g).

Provenance & Evidence