Dimethylformamide → HCID 86635018, compound

A mixture of 6-(3-fluoro-phenyl)-2H-[1,2,4]triazin-3-one (15.2 g, 79.5 mmol, crude) and 2 ml of DMF in 250 ml of 1:1 phosphorous oxychloride-chloroform was maintained at reflux overnight. The mixture was then concentrated at reduced pressure, diluted with methylene chloride and poured onto ice with stirring. When the ice melted the mixture was neutralized with sodium bicarbonate solution, and the layers were separated, the aqueous layer was extracted with dichloromethane once, the combined organic layer was washed with water, dried and concentrated to a brown oil which was purified by column chromatography (eluting with pure petroleum) to give title compound as a pale yellow solid (3.5 g, 21.0%): 1H NMR (CDCl3): δ 8.88 (s, 1H), 7.87-7.82 (m, 2H), 7.60-7.52 (m, 1H), 7.32-7.27 (m, 1H).

1. temperaturewas maintained
2. temperatureat reflux overnight
3. concentrationThe mixture was then concentrated at reduced pressure
4. additiondiluted with methylene chloride
5. additionpoured onto ice
6. customthe layers were separated
7. extractionthe aqueous layer was extracted with dichloromethane once
8. washthe combined organic layer was washed with water
9. customdried
10. concentrationconcentrated to a brown oil which
11. customwas purified by column chromatography (eluting with pure petroleum)

ORD record

ord-27d3d6d5c85c4fd3979869aae584ae2b

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507489B2