Azidotrimethylsilane → HCID 178509700, compound

3-[(E)-2-Nitroethenyl]benzonitrile (2.79 g, 16.0 mmol) and azidotrimethylsilane (2.76 g, 24.0 mmol) was stirred in anhydrous DMF (100 mL) at 50° C. To this was added tetrabutylammonium fluoride (17.6 mL of a 1.0M solution in THF, 17.6 mmol) via syringe pump over 20 min. The resulting reaction was quenched with MeOH (25 mL) and concentrated in vacuo to a volume of ca. 30 mL. The resulting crude mixture was dissolved in EtOAc (300 mL) and washed with H2O (2×100 mL). The product was then extracted from the EtOAc layer with 1M aqueous NaOH (4×75 mL). The combined basic aqueous portions were treated with 4M HCl to obtain an endpoint of pH=4, and the product was extracted into EtOAc (4×100 mL). The combined EtOAc extracts were dried (MgSO4), filtered and concentrated in vacuo to obtain 3-(1H-1,2,3-triazol-4-yl)benzonitrile as a tan solid.

1. customThe resulting reaction
2. customwas quenched with MeOH (25 mL)
3. concentrationconcentrated in vacuo to a volume of ca. 30 mL
4. dissolutionThe resulting crude mixture was dissolved in EtOAc (300 mL)
5. washwashed with H2O (2×100 mL)
6. extractionThe product was then extracted from the EtOAc layer with 1M aqueous NaOH (4×75 mL)
7. additionThe combined basic aqueous portions were treated with 4M HCl
8. customto obtain an endpoint of pH=4
9. extractionthe product was extracted into EtOAc (4×100 mL)
10. dry with materialThe combined EtOAc extracts were dried (MgSO4)
11. filtrationfiltered
12. concentrationconcentrated in vacuo

ORD record

ord-885792a93bfa466e84b5687b9e54e493

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105548B2