1H-1,2,4-Triazole → 4-(1H-1,2,4-triazol-1-yl)benzaldehyde

Temperature

105 °C

4-Fluorobenzaldehyde (12.0 mL, 112 mmol) was added dropwise by syringe to a stirring, heterogeneous mixture of 1,2,4-triazole (11.6 g, 168 mmol) and potassium carbonate (24.7 g, 179 mmol) in dimethyl formamide (220 mL) at 23° C. The mixture was heated to 105° C. After 3.5 hours, the mixture was allowed to cool to 23° C. The cooled solution was transferred to a 2 L Erlenmeyer flask and diluted with water (500 mL) and ethyl acetate (1200 mL). The biphasic mixture was stirred until the layers cleanly separated. The layers were separated. The organic layer was washed with half-saturated aqueous sodium chloride solution (3×100 mL). The washed solution was dried with sodium sulfate, and the dried solution was filtered. The filtrate was concentrated to provide an off-white solid. The solid was suspended in a mixture of heptanes and isopropyl acetate (5:1, 600 mL). The mixture was filtered and the filter cake was washed with heptanes-isopropyl acetate (5:1). The solids were collected and dried under vacuum to afford the titled compound as a white solid.

1. temperatureto cool to 23° C
2. customcleanly separated
3. customThe layers were separated
4. washThe organic layer was washed with half-saturated aqueous sodium chloride solution (3×100 mL)
5. dry with materialThe washed solution was dried with sodium sulfate
6. filtrationthe dried solution was filtered
7. concentrationThe filtrate was concentrated
8. customto provide an off-white solid
9. filtrationThe mixture was filtered
10. washthe filter cake was washed with heptanes-isopropyl acetate (5:1)
11. customThe solids were collected
12. customdried under vacuum

ORD record

ord-b2e790dcab284f06833232e528a29755

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290476B2