Réaction #2275722

Équation de réaction

sodium hydroxide

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

→

( 5 )

Rendement 50.0%

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

Rendement 50.0%

Solvants

water

ethanol

Conditions de réaction

Traitement

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
   Autrewere then partitioned
5. 5
   Extractionextracted twice with 70 ml of ethyl acetate
6. 6
   LavageThe ethyl acetate layer was washed with water
7. 7
   Séchagedried over anhydrous magnesium sulfate
8. 8
   Concentrationconcentrated
9. 9
   AutreThe residues were purified by silica gel chromatography (ethyl acetate: methanol=1:1)

Mode opératoire

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%).

Source