반응 #507394

반응 방정식

6-bromo-2-naphthoic acid

methylamine

triethylamine

thionyl chloride

→

6-bromo-N-methyl-2-naphthamide

수율 80.3%

용매

water

DMF

ethyl acetate

methanol

반응 조건

후처리

1. 1
   온도After cooled to 25° C.
2. 2
   workup.ADDITIONwas added dropwise at 25° C.
3. 3
   workup.STIRRINGThe mixture was stirred at 25° C. for 3 hours
4. 4
   여과Crystals were filtered
5. 5
   세척washed successively with 1.25 liters of a mixed solution of methanol/water=1/4
6. 6
   기타Vacuum drying (50° C.) to a constant weight

실험 절차

4 Liters of ethyl acetate and 25 mL of DMF were added to 500 g (1.99 mol) of 6-bromo-2-naphthoic acid. 188 mL (2.61 mol, 1.3 eq) of thionyl chloride was added dropwise at 30° C. or lower. The mixture was stirred at 65° C. for 30 minutes. After cooled to 25° C., a mixture of 408 mL (3.93 mol, 2 eq) of a 40% solution of methylamine in methanol and 558 mL (4.01 mol, 2 eq) of triethylamine was added dropwise at 25° C. or lower. The mixture was stirred at 25° C. for 3 hours. 2.5 Liters of water was added dropwise at 25° C. or lower. Crystals were filtered, and washed successively with 1.25 liters of a mixed solution of methanol/water=1/4. Vacuum drying (50° C.) to a constant weight afforded 422 g of 6-bromo-N-methyl-2-naphthamide (yield 80%).

출처