反応 #1596994

反応方程式

5-aminosalicylic acid

triethylamine

benzyl bromide

→

5-benzylaminosalylic acid

収率 113.8%

5-benzylaminosalicylic acid

収率 113.8%

溶媒

DMF

反応条件

後処理

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

実験手順

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).

出典