반응 #2461889

반응 방정식

triethylamine

HCl

2-acetylsalicyloyl chloride

NaOH

trimethylsilyl chloride

6-(2-aminobenzoylamino)hexanoic acid

→

6-[2-(2-hydroxybenzoylamino)benzoylamino]hexanoic acid

용매

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   기타the reaction
2. 2
   온도to reflux for 5 hours
3. 3
   기타the reaction
4. 4
   workup.STIRRINGcontinue stirring the mixture until the oil
5. 5
   여과filter the resulting solid
6. 6
   세척wash several times with water
7. 7
   기타Purify the reaction product
8. 8
   기타by recrystallization (EtOH/H2O)

실험 절차

To a suspension of 0.30 g (1.20 mmol) of 6-(2-aminobenzoylamino)hexanoic acid in 5 ml of dry methylene chloride, add 0.23 g (2.10 mmol) of trimethylsilyl chloride and allow the reaction to reflux for 5 hours. Then place the flask in an ice bath and add 0.15 g (1.53 mmol) of triethylamine and a solution of 0.20 g (2.05 mmol) of 2-acetylsalicyloyl chloride dissolved in 5 ml of dry methylene chloride. Allow the reaction to stir for 30 minutes in an ice bath and 24 hours at room temperature. Eliminate the solvent at low pressure, add 10 ml of 10% NaOH to the crude product and continue stirring the mixture until the oil has completely disappeared. Immediately acidify with concentrated HCl, filter the resulting solid and wash several times with water and with ether. Purify the reaction product by recrystallization (EtOH/H2O). This yields 0.24 g (62%) of 6-[2-(2-hydroxybenzoylamino)benzoylamino]hexanoic as a white solid.

출처