Reacción #640574

Ecuación de reacción

water

3-(2-Nitrobenzylamino)-1-phenylpropanol

triethylamine

triphosgene

→

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

Rendimiento 129.9%

Disolventes

toluene

toluene

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente