반응 #811384

반응 방정식

N-Ethyldiisopropylamine

methylamine

6-Bromo-2-naphthoic acid

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

1-hydroxy-1H-benzotriazole monohydrate

→

title compound

수율 95.6%

6-bromo-N-methyl-2-naphthamide

수율 95.6%

용매

water

THF

dimethylformamide

반응 조건

후처리

1. 1
   온도cooling
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 18 h
3. 3
   workup.STIRRINGwith stirring
4. 4
   여과the precipitate was collected by filtration
5. 5
   세척The precipitate was washed successively with water and diisopropyl ether
6. 6
   건조dried in the presence of phosphorus pentaoxide at 70° C.

실험 절차

6-Bromo-2-naphthoic acid (60.26 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (55.21 g) and 1-hydroxy-1H-benzotriazole monohydrate (44.1 g) were dissolved in dimethylformamide (960 ml) under an argon atmosphere. N-Ethyldiisopropylamine (37.23 g) was added with stirring under ice-cooling. A solution (2M; 192 ml) of methylamine in THF was added and the mixture was stirred at room temperature for 18 h. The reaction mixture was poured into water (8 L) with stirring and the precipitate was collected by filtration. The precipitate was washed successively with water and diisopropyl ether, and dried in the presence of phosphorus pentaoxide at 70° C. to give the title compound (60.6 g) as a crystalline powder.

출처