Sodium Hydroxide → N-(4,6-Bis(propylamino)-1,3,5-triazin-2-yl)-N,O-dimethylhydroxylamine

Temperature

60 °C

A mixture of 2-chloro-N-(4,6-bis-(n-propylamino)-[1,3,5]triazine (XXXIV) (10.00 g, 43.53 mmol), N,O-dimethylhydroxylamine hydrochloride (8.49 g, 87.06 mmol) and NaOH (3.13 g, 78.35 mmol) in 1,4-dioxane (120 mL) and water (30 mL) was heated at 60° C. for 6 h, after which the volatiles were removed under reduced pressure. Saturated NaHCO3 solution (500 mL) was added to the residue and the mixture was extracted with EtOAc (3×200 mL). The combined organic extracts were washed with water (300 mL), then with a brine solution (300 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the resultant residue was filtered through silica gel using eluent CH2Cl2/EtOH (9/1 v/v) to yield N-(4,6-bis-n-propylamino[1,3,5]triazine-2-yl)-N,O-dimethyl-hydroxylamine (XXXV) (9.96 g, 90% yield).

1. customafter which the volatiles were removed under reduced pressure
2. additionSaturated NaHCO3 solution (500 mL) was added to the residue
3. extractionthe mixture was extracted with EtOAc (3×200 mL)
4. washThe combined organic extracts were washed with water (300 mL)
5. dry with materialwith a brine solution (300 mL) and dried over Na2SO4
6. customThe solvent was removed under reduced pressure
7. filtrationthe resultant residue was filtered through silica gel using eluent CH2Cl2/EtOH (9/1 v/v)

ORD record

ord-1db5cde0ed5c44b1b94a75e79c21f748

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09162992B2