تفاعل #70066

معادلة التفاعل

benzoyl chloride

p-methoxybenzylamine

triethylamine

THF

→

N-(p-methoxybenzyl)benzamide

المردود 80.7%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   أخرىat 14° C.
2. 2
   استخلاصThe mixture was extracted with ethyl acetate (140 ml)
3. 3
   استخلاصthe aqueous layer was extracted with ethyl acetate (360 ml)
4. 4
   غسيلThe combined organic layers were washed successively with 20% brine (0.15 kg×2) and 20% brine (0.22 kg
5. 5
   تجفيفonce), and dried over magnesium sulfate (50 g)
6. 6
   workup.ADDITIONSilica gel (22 g) was added to the solution
7. 7
   ترشيحthe mixture was filtered (silica gel precoat)
8. 8
   تركيزThe filtrate was concentrated to 0.67 kg under reduced pressure at 60° C.
9. 9
   درجة الحرارةlower, and the residue was cooled to 5° C
10. 10
    ترشيحThe resulting crystals were collected by filtration
11. 11
    غسيلwashed with cold ethyl acetate (140 mL)
12. 12
    أخرىdried under reduced pressure at 50° C.

الإجراء التجريبي

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.

المصدر