Reaktion #1596994

Reaktionsgleichung

5-aminosalicylic acid

triethylamine

benzyl bromide

→

5-benzylaminosalylic acid

Ausbeute 113.8%

5-benzylaminosalicylic acid

Ausbeute 113.8%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONIce chips were added to the reaction mixture
2. 2
   Sonstigesolvent was removed in vacuo
3. 3
   workup.ADDITIONThe reaction mixture was diluted with water
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe organic layer was washed with water and brine
6. 6
   Trocknendried over anhydrous MgSO4
7. 7
   SonstigeAfter evaporation of the solvent
8. 8
   Sonstigethe residue was purified by column chromatography
9. 9
   Sonstigerecrystallized from methanol/ethyl acetate/hexane (1:3:1)

Vorschrift

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).

Quelle