Reaktion #70066

Reaktionsgleichung

benzoyl chloride

p-methoxybenzylamine

triethylamine

THF

→

N-(p-methoxybenzyl)benzamide

Ausbeute 80.7%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat 14° C.
2. 2
   ExtraktionThe mixture was extracted with ethyl acetate (140 ml)
3. 3
   Extraktionthe aqueous layer was extracted with ethyl acetate (360 ml)
4. 4
   WaschenThe combined organic layers were washed successively with 20% brine (0.15 kg×2) and 20% brine (0.22 kg
5. 5
   Trocknenonce), and dried over magnesium sulfate (50 g)
6. 6
   workup.ADDITIONSilica gel (22 g) was added to the solution
7. 7
   Filtrationthe mixture was filtered (silica gel precoat)
8. 8
   EinengenThe filtrate was concentrated to 0.67 kg under reduced pressure at 60° C.
9. 9
   Temperaturlower, and the residue was cooled to 5° C
10. 10
    FiltrationThe resulting crystals were collected by filtration
11. 11
    Waschenwashed with cold ethyl acetate (140 mL)
12. 12
    Sonstigedried under reduced pressure at 50° C.

Vorschrift

To a mixture of p-methoxybenzylamine (181 g, 1.32 mol), triethylamine (185 mL, 134 g, 1.32 mol) and THF (772 mL) was added dropwise benzoyl chloride (185 g, 1.32 mol) at 16° C. or lower. The mixture was stirred at 7° C. or lower for 3 hr, water (400 mL) was added dropwise thereto at 14° C. or lower. The mixture was extracted with ethyl acetate (140 ml), and the aqueous layer was extracted with ethyl acetate (360 ml). The combined organic layers were washed successively with 20% brine (0.15 kg×2) and 20% brine (0.22 kg, once), and dried over magnesium sulfate (50 g). Silica gel (22 g) was added to the solution, and the mixture was filtered (silica gel precoat). The filtrate was concentrated to 0.67 kg under reduced pressure at 60° C. or lower, and the residue was cooled to 5° C. The resulting crystals were collected by filtration, washed with cold ethyl acetate (140 mL), and dried under reduced pressure at 50° C. to give N-(p-methoxybenzyl)benzamide (257 g, yield 80.7%) as white crystals.

Quelle