Reacción #2275722

Ecuación de reacción

sodium hydroxide

ethyl 3-[5-(2-nitroiminoimidazolidin-1-ylmethyl)-2-pyridylthio]propionate

→

( 5 )

Rendimiento 50.0%

3-[5-(2-nitroiminoimidazolidin-1-ylmethyl)-2-pyridylthio]propionic acid

Rendimiento 50.0%

Disolventes

water

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added to a suspension
2. 2
   workup.DISTILLATIONThe ethanol was distilled away under reduced pressure, and 20 ml of water and 30 ml of ether
3. 3
   workup.ADDITIONwere added to the residues which
4. 4
   Otrowere then partitioned
5. 5
   Extracciónextracted twice with 70 ml of ethyl acetate
6. 6
   LavadoThe ethyl acetate layer was washed with water
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   Concentraciónconcentrated
9. 9
   OtroThe residues were purified by silica gel chromatography (ethyl acetate: methanol=1:1)

Procedimiento

0.44 g (11 mmol) of sodium hydroxide dissolved in 30 ml water was added to a suspension containing 1.3 g (3.7 mmol) of ethyl 3-[5-(2-nitroiminoimidazolidin-1-ylmethyl)-2-pyridylthio]propionate (4) in 40 ml of ethanol and stirred at room temperature for 1 hour. The ethanol was distilled away under reduced pressure, and 20 ml of water and 30 ml of ether were added to the residues which were then partitioned, and the aqueous layer was adjusted to pH 5 with dilute hydrochloric acid and extracted twice with 70 ml of ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residues were purified by silica gel chromatography (ethyl acetate: methanol=1:1) to give 0.6 g of (5) (yield 50%).

Fuente