1H-1,2,4-Triazole → 2-[1,2,4]triazol-1-yl-nicotinonitrile

Temperature

50 °C

A mixture of 2-chloro-nicotinonitrile (10.30 g, 74.4 mmol), 1H-[1,2,4]Triazole (5.36 g, 77.6 mmol), and Cs2CO3 (25.28 g, 77.6 mmol) in DMSO (30 mL) was stirred at 50° C. for C for 30 min. The resulting off-white semisolid was partitioned with water (600 mL) and DCM (600 mL), and the aq layer was extracted with DCM (2×200 mL). The combined organic layers were dried (Na2SO4), concentrated, and put under vacuum at 90° C. to remove the bulk of DMSO. The resulting white solid was briefly triturated with refluxing diethyl ether (100 mL), allowed to cool to rt, and filtered. The filter cake was washed with ether (3×50 mL) and dried to yield the title compound as white fluffy needles (11.37 g, 89%).

1. customThe resulting off-white semisolid was partitioned with water (600 mL) and DCM (600 mL)
2. extractionthe aq layer was extracted with DCM (2×200 mL)
3. dry with materialThe combined organic layers were dried (Na2SO4)
4. concentrationconcentrated
5. customput under vacuum at 90° C.
6. customto remove the bulk of DMSO
7. customThe resulting white solid was briefly triturated with refluxing diethyl ether (100 mL)
8. temperatureto cool to rt
9. filtrationfiltered
10. washThe filter cake was washed with ether (3×50 mL)
11. customdried

ORD record

ord-1d8f1299996e4f3a8aa7f4547e102c81

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07829584B2