Sodium Nitrate → Hydantoin, 5,5-dimethyl-3-(p-nitrophenyl)-

HRID 224946Notes

Reaction equation

HRID 224946 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[C:10]([CH3:14])([CH3:13])[NH:9][C:8]2=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:16]([O-])([O-:18])=[O:17].[Na+]>S(=O)(=O)(O)O>[N+:16]([C:4]1[CH:3]=[CH:2][C:1]([N:7]2[C:11](=[O:12])[C:10]([CH3:13])([CH3:14])[NH:9][C:8]2=[O:15])=[CH:6][CH:5]=1)([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 3054223Hydantoin, 5,5-dimethyl-3-phenyl-

Product 1

HCID 3054222Hydantoin, 5,5-dimethyl-3-(p-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  1. additionAfter the addition
  2. temperaturemaintained
  3. stirringstirring at 0° C.
  4. waitwas continued for 20 minutes with the reaction mixture
  5. temperatureto warm to room temperature
  6. stirringstirring
  7. waitwas continued for 4 hours
  8. additionThe mixture was then poured onto ice water
  9. extractionextracted with methylene chloride
  10. dry with materialThe extract was dried over sodium sulphate
  11. customThe methylene chloride was evaporated
  12. customthe resulting product was crystallized from methylene chloride/petroleum ether
  13. customThe recrystallized product was dried for 16 hours, under greatly reduced pressure

Sources & evidence

ORD record
ord-a0983554840f4e2ba2cf16776d84baeb
Source dataset
uspto-grants-1980_11
Patent number
US04234736

Reaction notes

Loading…