Potassium Cyanide → 5-(3-bromo-phenyl)-5-methyl-imidazolidine-2,4-dione

HRID 1041895Notes

Reaction equation

HRID 1041895 reaction equation
[C:1](=[O:4])([O-])[O-].[NH4+:5].[NH4+:6].[C-]#N.[K+].[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=1)=O.C[CH2:21][OH:22].O>O>[Br:19][C:15]1[CH:14]=[C:13]([C:11]2([CH3:10])[NH:6][C:21](=[O:22])[NH:5][C:1]2=[O:4])[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 9032Potassium CyanideHCID 165023'-BromoacetophenoneHCID 517111Ammonium CarbonateHCID 19096565Water ethanol

Product 1

HCID 2433325-(3-bromo-phenyl)-5-methyl-imidazolidine-2,4-dioneYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a suspension of ammonium carbonate (20.5 g, 225 mmol) and potassium cyanide (8.6 g, 125 mmol) in EtOH/water (160 mL, 1/1) at 23° C. was added 3-bromoacetophenone (6.61 mL, 50 mmol). The pressure-tube was sealed and heated for 24 h at 95° C., then cooled to 23° C. The solution was diluted with water (300 mL), the solid removed by filtration and dried under vacuum to give the desired material (11.3 g, 84%). MS (ES+): 269/271 (M+H), 310/312 (M+H+ CH3CN).

Workup

  1. customThe pressure-tube was sealed
  2. temperaturecooled to 23° C
  3. customthe solid removed by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f7aa4b2460724aa598e1c0dba5fc2962
Source dataset
uspto-grants-2013_10
Patent number
US08557798B2

Reaction notes

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