Benzaldehyde → 1-Hydroxy-3-benzylidenetriazene

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).

1. temperaturecooling
2. extractionthe resultant mixture was extracted with chloroform
3. dry with materialdried over anhydrous magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. customto give a residue, which
6. stirringThe reaction mixture was stirred for 2 hours at ambient temperature
7. customInsoluble materials were removed by filtration
8. concentrationThe filtrate was concentrated under reduced pressure
9. customto give a residue
10. customThe organic layer was separated
11. washwashed with water
12. dry with materialdried over magnesium sulfate
13. concentrationconcentrated under reduced pressure

ORD record

ord-f68e6a62b1ee4f5b8eecb6fb63c30648

Source dataset

uspto-grants-1981_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04297096