Reaction #2275722

Reaction equation

sodium hydroxide

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

→

( 5 )

Yield 50.0%

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

Yield 50.0%

Solvents

water

ethanol

Conditions

Workup

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

Procedure

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