Reaktion #312128

Reaktionsgleichung

3-phenyl-5,5-dimethylhydantoin

sodium nitrate

→

3-(4-nitrophenyl)-5,5-dimethylhydantoin

Lösungsmittel

sulphuric acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturmaintained
3. 3
   workup.STIRRINGstirring at 0° C.
4. 4
   workup.WAITwas continued for 20 minutes with the reaction mixture
5. 5
   Temperaturto warm to room temperature
6. 6
   workup.STIRRINGstirring
7. 7
   workup.WAITwas continued for 4 hours
8. 8
   workup.ADDITIONThe mixture was then poured onto ice water
9. 9
   Extraktionextracted with methylene chloride
10. 10
    TrocknenThe extract was dried over sodium sulphate
11. 11
    SonstigeThe methylene chloride was evaporated
12. 12
    Sonstigethe resulting product was crystallized from methylene chloride/petroleum ether
13. 13
    SonstigeThe recrystallized product was dried for 16 hours, under greatly reduced pressure

Vorschrift

17.0 g (83 mmol) of 3-phenyl-5,5-dimethylhydantoin were dissolved in 160 ml of concentrated sulphuric acid and 7.07 g (83 mmol) of sodium nitrate were slowly added with stirring, at 0° C. over a 40 minute period. After the addition was completed, maintained stirring at 0° C. was continued for 20 minutes with the reaction mixture. The mixture was allowed to warm to room temperature and stirring was continued for 4 hours. The mixture was then poured onto ice water and then extracted with methylene chloride. The extract was dried over sodium sulphate. The methylene chloride was evaporated and the resulting product was crystallized from methylene chloride/petroleum ether. The recrystallized product was dried for 16 hours, under greatly reduced pressure, to yield 3-(4-nitrophenyl)-5,5-dimethylhydantoin, m.p. 176°-177° C.

Quelle