Hydrochloric Acid → 5-(4-Bromophenyl)-5-phenylimidazolidine-2,4-dione

HRID 1659542Notes

Reaction equation

HRID 1659542 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.[C:16](=[O:19])([O-])[O-].[NH4+:20].[NH4+].[C-]#N.[K+].Cl.[OH-].[Na+].C[N:29](C)[CH:30]=[O:31]>O>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]2([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[NH:20][C:30](=[O:31])[NH:29][C:16]2=[O:19])=[CH:4][CH:3]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 70304-BromobenzophenoneHCID 9032Potassium CyanideHCID 14798Sodium HydroxideHCID 517111Ammonium Carbonate

Product 1

HCID 130192725-(4-Bromophenyl)-5-phenylimidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

In a 500 ml steel bomb, 60 gr of 4-bromobenzophenone in 300 ml of dimethylformamide, 100 gr of solid ammonium carbonate and 30 gr of potassium cyanide in 100 ml of water are added. After closing the bomb, the reaction mixture is heated to 120° C. for 5 days, then poured under fast mechanical stirring into 2 l of water at 80° C., then acidified (concentrated HCl) and centrifuged after cooling in an ice-bath. A crude product is obtained, which is treated with 2 N sodium hydroxide (500 ml). The suspension is filtered; the filtrate is extracted three times with ether (total of 300 ml). The aqueous phase is acidified with concentrated hydrochloric acid to give 59 gr of 5-(parabromophenyl)-5-phenylhydantoin as a crude product. A recrystallization from ethanol gives 40 gr of pure product.

Workup

  1. additionpoured
  2. temperatureafter cooling in an ice-bath
  3. customA crude product is obtained
  4. filtrationThe suspension is filtered
  5. extractionthe filtrate is extracted three times with ether (total of 300 ml)

Sources & evidence

ORD record
ord-9038b4bc1b714c759acf463975b4a06b
Source dataset
uspto-grants-1981_12
Patent number
US04304782

Reaction notes

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