Reaction #50920

Reaction equation

2-chloro-5-nitropyridine

thiomorpholine

→

title compound

4-(5-Nitro-pyridin-2-yl)-thiomorpholine

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was refluxed for additional 2 h
2. 2
   Otherthe solvent was removed in vacuo
3. 3
   workup.DISSOLUTIONthe residue was re-dissolved in 200 ml ethyl acetate
4. 4
   WashThe organic phase was washed with 200 ml 1 N sodium bicarbonate solution
5. 5
   Dryingdried (magnesium sulfate)
6. 6
   Otherevaporated

Procedure

To a solution of 20 g (126 mmol) of 2-chloro-5-nitropyridine in 200 ml tetrahydrofuran were added dropwise 32.5 ml (315 mmol) thiomorpholine within 10 min. The reaction mixture was refluxed for additional 2 h. After cooling to room temperature, the solvent was removed in vacuo and the residue was re-dissolved in 200 ml ethyl acetate. The organic phase was washed with 200 ml 1 N sodium bicarbonate solution, dried (magnesium sulfate) and evaporated to give 29.3 g (quantitative) of the title compound as a yellow solid.

Source