Réaction #2186208

Équation de réaction

sodium bicarbonate

3-Benzothiazol-2-yl-7-[4-(3-hydroxy-propyl)-piperazin-1-yl]-chromen-2-one

Hünig base

tosyl chloride

→

Toluene-4-sulfonic acid 3-[4-(3-benzothiazol-2-yl-2-oxo-2H-chromen-7-yl)-piperazin-1-yl]-propyl ester

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONpoured onto ice
2. 2
   Extractionextracted (dichloromethane, saline)
3. 3
   AutreThe organic phase is evaporated
4. 4
   Autrethe residue column chromatographed (silica gel, dichloromethane/EtOH 98:2)
5. 5
   Autreto yield
6. 6
   Autreafter evaporation
7. 7
   Séchagedrying under high vacuum 73 mg (78%) desired product as a light brownish powder

Mode opératoire

70 mg (0.16 mmol) 3-Benzothiazol-2-yl-7-[4-(3-hydroxy-propyl)-piperazin-1-yl]-chromen-2-one are dissolved in 15 mL dichloromethane under argon. 0.083 mL Hünig base and 10 mg DMAP are added to the stirred solution, followed by 46 mg (1.5 eq.) tosyl chloride. The reaction mixture is stirred for 20 h at room temperature, poured onto ice, treated with 2 mL aqueous sodium bicarbonate solution and extracted (dichloromethane, saline). The organic phase is evaporated and the residue column chromatographed (silica gel, dichloromethane/EtOH 98:2) to yield after evaporation and drying under high vacuum 73 mg (78%) desired product as a light brownish powder.

Source