Butyl nitrite → 3,3-Dimethoxy-2-hydroxyiminopropionitrile

To a flask having an inner volume of 100 ml and equipped with a stirring device and a dropping funnel were charged 3.0 g (36 mmol) of 3-methoxyacrylonitrile, 9.0 g (63 mmol) of a 25.7% by weight hydrogen chloride methanol solution and 15 ml of methanol. Under stirring, 4.7 g (43 mmol) of n-butyl nitrite was gradually added dropwise to the mixture to generate nitrosyl halide and n-butyl alcohol in the system (the method of the above-mentioned (1)), and the mixture was reacted at room temperature for 26 hours. After completion of the reaction, a saturated sodium hydrogen carbonate was added to the mixture to neutralize the mixture, and methanol was removed from the reaction mixture by distillation under reduced pressure. The aqueous layer was extracted with ethyl acetate, the organic layer was taken out, washed with a saturated saline solution, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, the concentrate was recrystallized from toluene to obtain 2.6 g of 3,3-dimethoxy-2-hydroxyiminopropionitrile (Isolation yield: 50%) as white solid.

1. customTo a flask having
2. customan inner volume of 100 ml and equipped with a stirring device and a dropping funnel
3. customwas reacted at room temperature for 26 hours
4. customAfter completion of the reaction
5. customwas removed from the reaction mixture by distillation under reduced pressure
6. extractionThe aqueous layer was extracted with ethyl acetate
7. washwashed with a saturated saline solution
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationAfter filtration
10. concentrationthe filtrate was concentrated under reduced pressure
11. customthe concentrate was recrystallized from toluene

ORD-Eintrag

ord-0aa1c505f4a543eca550ff9d4c8200ad

Quelldatensatz

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07227032B2