1H-1,2,4-Triazole → HCID 63778647, compound

Sodium hydride (60 wt. %. in mineral oil, 400 mg, 10.0 mmol, 5.0 eq) was carefully suspended in 5 mL of DMA (caution: intensive gas development). To the mixture was added carefully 1,2,4-triazole (691 mg, 10.0 mmol, 5.0 eq) and the mixture was stirred at room temperature for 30 min. 2,4-Dichloropyridine (300 mg, 2.0 mmol, 1.0 eq) was added in portions and the reaction mixture was heated at 100° C. for 3.5 hours. The mixture was allowed to cool to room temperature and diluted with saturated NaCl solution (25 mL) and EtOAc (15 mL). The separated aqueous layer was extracted with EtOAc (3×25 mL) and the combined organic layers were washed with saturated NaCl solution (25 mL), dried over sodium sulfate and concentrated under reduced pressure. Purification by silica column chromatography with EtOAc/hexanes (3/1) provided 2-chloro-4-(1H-1,2,4-triazol-1-yl)pyridine as a white solid. Yield: 290 mg. ES/MS m/z 181.1 (MH+).

1. temperaturethe reaction mixture was heated at 100° C. for 3.5 hours
2. temperatureto cool to room temperature
3. extractionThe separated aqueous layer was extracted with EtOAc (3×25 mL)
4. washthe combined organic layers were washed with saturated NaCl solution (25 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customPurification by silica column chromatography with EtOAc/hexanes (3/1)

ORD record

ord-371f1ce60cfb47e19fa3f2a228213215

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293769B2