Methanol → 2-(4-Chloro-butyl)-2H-[1,2,4]triazine-3,5-dione

22.1 g of 3,5-Bis-trimethylsilanyloxy-[1,2,4]triazine (86 mmol) were dissolved in 150 mL of dichloroethane followed by addition of 14.7 g of 1-bromo-4-chloro-butane (86 mmol) and 0.218 g of iodine (0.858 mmol). The reaction mixture was stirred for 25 h at room temperature. Then, 300 mL of methanol were added and the mixture was stirred for an additional 10 minutes. The solvents were evaporated under reduced pressure and the residue was partitioned between dichloromethane and water. The aqueous phase was extracted several times with dichloromethane. The combined organic layers were washed with 10% aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and the organic phase was evaporated under reduced pressure. The thus obtained crude product was purified via silica gel chromatography using dichloromethane-methanol 0-10% to yield 13.4 g of the desired product.

1. stirringthe mixture was stirred for an additional 10 minutes
2. customThe solvents were evaporated under reduced pressure
3. customthe residue was partitioned between dichloromethane and water
4. extractionThe aqueous phase was extracted several times with dichloromethane
5. washThe combined organic layers were washed with 10% aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customthe organic phase was evaporated under reduced pressure
9. customThe thus obtained crude product
10. customwas purified via silica gel chromatography

ORD-Eintrag

ord-53ded76454e04703a7aef4522fde93ca

Quelldatensatz

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08492540B2