반응 #76093

반응 방정식

(4-bromo-phenyl)-acetic acid

thionyl chloride

heptylamine

N,N-diisopropylethylamine

→

2-(4-bromo-phenyl)-N-heptyl-acetamide

용매

chloroform

methylene chloride

methylene chloride

water

반응 조건

후처리

1. 1
   온도under reflux for 20 hours
2. 2
   기타evaporated under vacuum
3. 3
   기타to give an oil
4. 4
   온도cooled to 0° C
5. 5
   추출extracted with methylene chloride
6. 6
   세척The extract was washed with saturated brine
7. 7
   건조dried over anhydrous sodium sulfate
8. 8
   기타the solvent was removed under vacuum
9. 9
   기타The solid residue was purified by crystallization from ethyl acetate/hexanes

실험 절차

A stirred solution of (4-bromo-phenyl)-acetic acid (0.186 mol, 40.0 g) and thionyl chloride (0.558 mol, 40.0 mL) in chloroform (500 mL) under a N2 atmosphere was heated under reflux for 20 hours. The mixture was cooled to room temperature and evaporated under vacuum to give an oil. This was dissolved in anhydrous methylene chloride (150 mL) and added dropwise to a solution of heptylamine (0.20 mol, 30.3 mL) and N,N-diisopropylethylamine (0.37 mol, 64.7 mL) in anhydrous methylene chloride cooled to 0° C. The mixture was stirred at room temperature for 45 minutes then poured into water and extracted with methylene chloride. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and the solvent was removed under vacuum. The solid residue was purified by crystallization from ethyl acetate/hexanes to give 2-(4-bromo-phenyl)-N-heptyl-acetamide as a white solid. (37 g, 64%)

출처