Reacción #5556

Ecuación de reacción

benzenesulfonyl chloride

5-[3-(amino)propyloxy]imidazo[1,2-a]pyridine dihydrochloride

triethylamine

acetonitrile

→

desired product

Rendimiento 59.5%

5-[3-(benzenesulfonamido)propyloxy]imidazo[1,2-a]pyridine

Rendimiento 59.5%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 1 hour
3. 3
   LavadoThe reaction mixture was washed in turn with an aqueous sodium bicarbonate solution and saturated saline
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONAfter the solvent was distilled off
6. 6
   Otrothe crude product thus obtained
7. 7
   Otrowas recrystallized from methylene-ethanol

Procedimiento

To a suspension of 5-[3-(amino)propyloxy]imidazo[1,2-a]pyridine dihydrochloride (2.64 g, 10 mmoles) and triethylamine (4.88 ml, 35 mmoles) in methylene chloride (100 ml)-acetonitrile (30 ml) was added benzenesulfonyl chloride (1.53 ml, 12 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 1 hour. The reaction mixture was washed in turn with an aqueous sodium bicarbonate solution and saturated saline and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the crude product thus obtained was recrystallized from methylene-ethanol to obtain 1.97 g of the desired product (59.5%, light brown crystals).

Fuente