反応 #76093

反応方程式

(4-bromo-phenyl)-acetic acid

thionyl chloride

heptylamine

N,N-diisopropylethylamine

→

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

溶媒

chloroform

methylene chloride

methylene chloride

water

反応条件

後処理

1. 1
   温度under reflux for 20 hours
2. 2
   その他evaporated under vacuum
3. 3
   その他to give an oil
4. 4
   温度cooled to 0° C
5. 5
   抽出extracted with methylene chloride
6. 6
   洗浄The extract was washed with saturated brine
7. 7
   乾燥dried over anhydrous sodium sulfate
8. 8
   その他the solvent was removed under vacuum
9. 9
   その他The solid residue was purified by crystallization from ethyl acetate/hexanes

実験手順

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%)

出典