반응 #69466

반응 방정식

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

수율 50.3%

용매

DCM

water

water

반응 조건

후처리

1. 1
   여과The reaction was filtered
2. 2
   기타to remove insoluble particles
3. 3
   기타transferred into a vessel
4. 4
   workup.ADDITIONcontaining water (2 L) (vessel 1)
5. 5
   기타adjusted to approximately 7° C.
6. 6
   온도to maintain the contents at 10° C.
7. 7
   workup.STIRRINGthe contents agitated for 4 hours
8. 8
   기타The contents of vessel 2 was transferred to vessel
9. 9
   workup.STIRRING1 and agitated at room temperature overnight
10. 10
    추출extracted with a further portion of DCM
11. 11
    건조dried (Na2SO4)
12. 12
    기타evaporated to dryness
13. 13
    workup.STIRRINGThe solid was stirred in ethyl acetate
14. 14
    여과filtered

실험 절차

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.

출처