Benzoyl chloride → N-[(4-methoxyphenyl)methyl]benzamide

Temperatur

7 °C

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.

1. customat 14° C.
2. extractionThe mixture was extracted with ethyl acetate (140 ml)
3. extractionthe aqueous layer was extracted with ethyl acetate (360 ml)
4. washThe combined organic layers were washed successively with 20% brine (0.15 kg×2) and 20% brine (0.22 kg
5. dry with materialonce), and dried over magnesium sulfate (50 g)
6. additionSilica gel (22 g) was added to the solution
7. filtrationthe mixture was filtered (silica gel precoat)
8. concentrationThe filtrate was concentrated to 0.67 kg under reduced pressure at 60° C.
9. temperaturelower, and the residue was cooled to 5° C
10. filtrationThe resulting crystals were collected by filtration
11. washwashed with cold ethyl acetate (140 mL)
12. customdried under reduced pressure at 50° C.

ORD-Eintrag

ord-8a356817582d42e59d5108533dcada2d

Quelldatensatz

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08530506B2