反应 #1596994

反应方程式

5-aminosalicylic acid

triethylamine

benzyl bromide

→

5-benzylaminosalylic acid

收率 113.8%

5-benzylaminosalicylic acid

收率 113.8%

溶剂

DMF

反应条件

后处理

1. 1
   workup.ADDITIONIce chips were added to the reaction mixture
2. 2
   其他solvent was removed in vacuo
3. 3
   workup.ADDITIONThe reaction mixture was diluted with water
4. 4
   萃取extracted with ethyl acetate
5. 5
   洗涤The organic layer was washed with water and brine
6. 6
   干燥dried over anhydrous MgSO4
7. 7
   其他After evaporation of the solvent
8. 8
   其他the residue was purified by column chromatography
9. 9
   其他recrystallized from methanol/ethyl acetate/hexane (1:3:1)

实验过程

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).

来源