Cyanuric chloride → 2,4-Dichloro-6-methyl-1,3,5-triazine

Methyl magnesium bromide (3M in ethyl ether, 9 ml, 27 mmol) was added dropwise over 10 min to a cooled (0° C.) solution of 2,4,6-trichloro-1,3,5-triazine (5 g, 27 mmol) in tetrahydrofuran (270 ml). The reaction mixture was stirred at ambient temperature for 20 hours and was then quenched with saturated NH4Cl (aq) (100 mL). The aqueous layer was extracted using dichloromethane (3×50 mL), and the combined organic layers were dried over Na2SO4, filtered, and concentrated to remove the most of solvent. Celite was then added to the solution and the resulting suspension was concentrated to dryness under vacuum and purified using silica gel chromatography (120 g SiO2 gel column; solvent dichloromethane/hexane from 0 to 30%) to give 2,4-dichloro-6-methyl-1,3,5-triazine (1.38 g of 90% purity, 7.57 mmol, 28%). MS (ES) m/e 164 [M+H]+.

1. customwas then quenched with saturated NH4Cl (aq) (100 mL)
2. extractionThe aqueous layer was extracted
3. dry with materialthe combined organic layers were dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customto remove the most of solvent
7. additionCelite was then added to the solution
8. concentrationthe resulting suspension was concentrated to dryness under vacuum
9. custompurified

ORD record

ord-e2fc723307614e51ad20d93962ab1190

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08008483B2