Reaktion #69466

Reaktionsgleichung

KOH

methyl 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylate

2-chloro-4,6-dimethoxy-1,3,5-triazine

4-methylmorpholine

Morpholine

→

8-bromo-6-(morpholine-4-carbonyl)-2-morpholino-4H-chromen-4-one

Ausbeute 50.3%

Lösungsmittel

DCM

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction was filtered
2. 2
   Sonstigeto remove insoluble particles
3. 3
   Sonstigetransferred into a vessel
4. 4
   workup.ADDITIONcontaining water (2 L) (vessel 1)
5. 5
   Sonstigeadjusted to approximately 7° C.
6. 6
   Temperaturto maintain the contents at 10° C.
7. 7
   workup.STIRRINGthe contents agitated for 4 hours
8. 8
   SonstigeThe contents of vessel 2 was transferred to vessel
9. 9
   workup.STIRRING1 and agitated at room temperature overnight
10. 10
    Extraktionextracted with a further portion of DCM
11. 11
    Trocknendried (Na2SO4)
12. 12
    Sonstigeevaporated to dryness
13. 13
    workup.STIRRINGThe solid was stirred in ethyl acetate
14. 14
    Filtrationfiltered

Vorschrift

KOH (0.419 L, 4889 mmol) was added portionwise to methyl 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylate (900 g, 2444 mmol) in water (5 L) at 20° C. over a period of 1 hour. The resulting suspension was stirred at 20° C. for 4 hours until saponification was complete. The reaction was filtered to remove insoluble particles and transferred into a vessel containing water (2 L) (vessel 1). Morpholine (0.639 L, 7333 mmol) was added and agitation continued. 2-chloro-4,6-dimethoxy-1,3,5-triazine (1931 g, 11000 mmol) and water (8 L) was charged to vessel 2 and the temperature adjusted to approximately 7° C., 4-methylmorpholine (134 mL, 1222 mmol) was charged at a rate to maintain the contents at 10° C. and the contents agitated for 4 hours. The contents of vessel 2 was transferred to vessel 1 and agitated at room temperature overnight. DCM (5 L) was then added and the mixture transferred to a 30 litre separator, extracted with a further portion of DCM and the organic extracts combined, dried (Na2SO4) and evaporated to dryness. The solid was stirred in ethyl acetate and filtered to give 8-bromo-6-(morpholine-4-carbonyl)-2-morpholino-4H-chromen-4-one (520 g, 50.3%) as a slightly grey solid. Mass Spectrum: m/z [M+H]+=425.

Quelle