Reaction #640574

Reaction equation

water

3-(2-Nitrobenzylamino)-1-phenylpropanol

triethylamine

triphosgene

→

3-(2-nitrobenzyl)-6-phenyl-[1,3]-oxazinan-2-one

Yield 129.9%

Solvents

toluene

toluene

Conditions

Workup

1. 1
   workup.ADDITIONwas slowly added dropwise
2. 2
   Temperatureheated
3. 3
   Temperatureto reflux for six hours
4. 4
   Temperatureto cool
5. 5
   Extractionextracted with ethyl acetate
6. 6
   WashThe organic layer was washed with 0.1N hydrochloric acid water
7. 7
   Dryingdried over anhydrous sodium sulfate
8. 8
   Otherthe solvent was evaporated under reduced pressure
9. 9
   WashThe residue was washed with a mixture of ether-ethyl acetate (1:2)

Procedure

3-(2-Nitrobenzylamino)-1-phenylpropanol (3.00 g, 10.5 mmol), triethylamine (4.24 g, 42.0 mmol) were dissolved in toluene (50 ml). Under ice cooled condition, a solution in which triphosgene (1.24 g, 4.19 mmol) was dissolved in toluene (5 ml) was slowly added dropwise thereto and heated to reflux for six hours after stirred at room temperature for one hour. The reaction mixture was poured into water and, after standing to cool, extracted with ethyl acetate. The organic layer was washed with 0.1N hydrochloric acid water and then dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was washed with a mixture of ether-ethyl acetate (1:2) to obtain 3-(2-nitrobenzyl)-6-phenyl-[1,3]-oxazinan-2-one (1.70 g).

Source