반응 #1596994

반응 방정식

5-aminosalicylic acid

triethylamine

benzyl bromide

→

5-benzylaminosalylic acid

수율 113.8%

5-benzylaminosalicylic acid

수율 113.8%

용매

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONIce chips were added to the reaction mixture
2. 2
   기타solvent was removed in vacuo
3. 3
   workup.ADDITIONThe reaction mixture was diluted with water
4. 4
   추출extracted with ethyl acetate
5. 5
   세척The organic layer was washed with water and brine
6. 6
   건조dried over anhydrous MgSO4
7. 7
   기타After evaporation of the solvent
8. 8
   기타the residue was purified by column chromatography
9. 9
   기타recrystallized from methanol/ethyl acetate/hexane (1:3:1)

실험 절차

To a solution of 5-aminosalicylic acid (2.0 g, 13 mmole, purchased from Aldrich Chemical Company, USA) and triethylamine in dried DMF (25 ml) was added benzyl bromide (2.68 g, 1.90 ml, 15.6 mmole) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred for 4 hr at room temperature. Ice chips were added to the reaction mixture and then solvent was removed in vacuo. The reaction mixture was diluted with water and then extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous MgSO4. After evaporation of the solvent, the residue was purified by column chromatography and recrystallized from methanol/ethyl acetate/hexane (1:3:1) to give 3.6 g (73% yield) of 5-benzylaminosalylic acid as a white solid.:mp 173.5-174.5° C. (decompose).

출처