反応 #69466

反応方程式

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

収率 50.3%

溶媒

DCM

water

water

反応条件

後処理

1. 1
   ろ過The reaction was filtered
2. 2
   その他to remove insoluble particles
3. 3
   その他transferred into a vessel
4. 4
   workup.ADDITIONcontaining water (2 L) (vessel 1)
5. 5
   その他adjusted to approximately 7° C.
6. 6
   温度to maintain the contents at 10° C.
7. 7
   workup.STIRRINGthe contents agitated for 4 hours
8. 8
   その他The contents of vessel 2 was transferred to vessel
9. 9
   workup.STIRRING1 and agitated at room temperature overnight
10. 10
    抽出extracted with a further portion of DCM
11. 11
    乾燥dried (Na2SO4)
12. 12
    その他evaporated to dryness
13. 13
    workup.STIRRINGThe solid was stirred in ethyl acetate
14. 14
    ろ過filtered

実験手順

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.

出典