Reaktion #70072

Reaktionsgleichung

sodium carbonate

benzoyl chloride

o-methoxybenzylamine

→

N-benzoyl-2-methoxybenzylamine

Lösungsmittel

water

water

toluene

toluene

hexane ethyl acetate

water

dichloromethane

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONDuring addition dropwise
2. 2
   workup.STIRRINGto stir the mixture
3. 3
   Temperaturto warm to room temperature
4. 4
   workup.STIRRINGstirred for 20 min
5. 5
   TemperaturThe reaction mixture was cooled to 3° C.
6. 6
   Filtrationfiltered
7. 7
   workup.ADDITIONTo the solid was added city water (800 mL)
8. 8
   workup.STIRRINGthe mixture was stirred for 7.5 hr
9. 9
   Filtrationfiltered
10. 10
    EinengenThe organic layer of the mother liquor was concentrated to dryness
11. 11
    FiltrationThe solid collected by filtration
12. 12
    Filtrationthe suspension was filtered
13. 13
    Einengenthe filtrate was concentrated to dryness
14. 14
    FiltrationThe solid collected by filtration
15. 15
    Sonstigethe residue obtained by concentration to dryness of the organic layer of the above-mentioned mother liquor
16. 16
    workup.ADDITIONwere mixed
17. 17
    Sonstigethe organic layer was separated
18. 18
    WaschenThe organic layer was washed successively with 1 mol/L hydrochloric acid (600 mL), water (600 mL) and 20% brine (600 mL)
19. 19
    Trocknendried over magnesium sulfate (60 g)
20. 20
    FiltrationThe magnesium sulfate was filtered off
21. 21
    Einengenthe filtrate was concentrated under reduced pressure in a bath at 50° C.
22. 22
    Sonstigewas decreased to 18° C
23. 23
    FiltrationThe solid was collected by filtration
24. 24
    Waschenwashed with cold dichloromethane (85 mL)
25. 25
    Sonstigedried under reduced pressure at 50° C.

Vorschrift

To a solution of sodium carbonate (232 g, 2.19 mol) in water (750 mL) were added toluene (750 mL) and water (750 mL), the mixture was cooled to 9° C., and o-methoxybenzylamine (300 g, 2.19 mol) was added thereto. To the mixture was added dropwise benzoyl chloride (307 g, 2.19 mol) with stirring at 3-8° C. During addition dropwise, toluene (750 mL) was added thereto to stir the mixture. The reaction mixture was allowed to warm to room temperature, and stirred for 20 min. The reaction was monitored by TLC (eluent: hexane/ethyl acetate (1:1)). The reaction mixture was cooled to 3° C., and filtered. To the solid was added city water (800 mL), and the mixture was stirred for 7.5 hr, and filtered. The organic layer of the mother liquor was concentrated to dryness. The solid collected by filtration was suspended in toluene (600 mL), the suspension was filtered, and the filtrate was concentrated to dryness. The solid collected by filtration, the residue obtained by concentration to dryness of the organic layer of the above-mentioned mother liquor, the residue obtained by concentration to dryness of the filtrate of the toluene suspension, dichloromethane (1500 mL) and water (1500 mL) were mixed, and the organic layer was separated. The organic layer was washed successively with 1 mol/L hydrochloric acid (600 mL), water (600 mL) and 20% brine (600 mL), and dried over magnesium sulfate (60 g). The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure in a bath at 50° C. or lower (about 830 g), and the bath temperature was decreased to 18° C. The solid was collected by filtration, washed with cold dichloromethane (85 mL), and dried under reduced pressure at 50° C. or lower to give N-benzoyl-2-methoxybenzylamine (the primary crystals 481 g, 91.2%) as white crystals. As a result of HPLC analysis, the area percentage was 99.3%, and the content was 97.8%.

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