Reaktion #216083

Reaktionsgleichung

2-(5-carboxymethylthio-4-chloro -2-fluorophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione

N,N-diethylhydroxylamine

→

2-[5-(N,N-diethylaminooxycarbonylmethylthio)-4-chloro-2-fluorophenyl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione

Ausbeute 72.5%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   SonstigeAfter completion of the reaction
3. 3
   workup.ADDITIONthe reaction mixture was poured into a saturated saline solution
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe extract was washed with a saturated saline solution
6. 6
   Trocknendried with anhydrous magnesium sulfate
7. 7
   Sonstigeevaporated
8. 8
   Sonstigeto remove the solvent under reduced pressure
9. 9
   SonstigeThe residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=5:1 to 3:1), which

Vorschrift

In 20 ml of tetrahydrofuran, 1.85 g of 2-(5-carboxymethylthio-4-chloro -2-fluorophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione was dissolved, to which 0.97 g of N,N'-carbonyldiimidazole was added and the resultant mixture was stirred for 30 minutes at room temperature. To the resultant mixture, 0.53 g of N,N-diethylhydroxylamine was added, and the resultant mixture was stirred for 2 hours at room temperature. After completion of the reaction, the reaction mixture was poured into a saturated saline solution and extracted with ethyl acetate. The extract was washed with a saturated saline solution, dried with anhydrous magnesium sulfate, and evaporated to remove the solvent under reduced pressure. The residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=5:1 to 3:1), which afforded 1.60 g of 2-[5-(N,N-diethylaminooxycarbonylmethylthio)-4-chloro-2-fluorophenyl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione.

Quelle