Reaction #640581

Reaction equation

5,5-Dimethyl-3-(2-nitrobenzyl)-[1,3]-oxazinan-2-thione

ammonium chloride

water

→

3-(2-aminobenzyl)-5,5-dimethyl-[1,3]-oxazinan-2-thione

Yield 63.2%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperatureto reflux for one hour
2. 2
   Filtrationthe reaction mixture was filtered with suction
3. 3
   Extractionextracted with ethyl acetate
4. 4
   WashThe organic layer was washed with a saturated brine
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   Otherthe solvent was evaporated under reduced pressure

Procedure

5,5-Dimethyl-3-(2-nitrobenzyl)-[1,3]-oxazinan-2-thione (1.06 g, 3.79 mmol), iron powder (1.06 g, 19.0 mmol), ammonium chloride (0.10 g, 1.87 mmol) were suspended in ethanol (20 ml) and water (10 ml) and heated to reflux for one hour. After cooling to room temperature, the reaction mixture was filtered with suction and extracted with ethyl acetate. The organic layer was washed with a saturated brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 3-(2-aminobenzyl)-5,5-dimethyl-[1,3]-oxazinan-2-thione (0.60 g).

Source