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

HRID 71683

Reaction equation

HRID 71683 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)=O.[C:11](=[O:14])([O-])[O-].[NH4+:15].[NH4+:16].[C-]#N.[K+].Cl.[CH2:21]([OH:23])C>O>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]2([CH3:1])[NH:16][C:21](=[O:23])[NH:15][C:11]2=[O:14])=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7466p-BromoacetophenoneHCID 9032Potassium CyanideHCID 517111Ammonium Carbonate

Product 1

HCID 2331105-(4-Bromophenyl)-5-methylimidazolidine-2,4-dioneYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 4-bromo acetophenone (8.0 g, 40.2 mmol), ammonium carbonate (40 g, 402 mmol) and potassium cyanide (3.4 g, 52.3 mmol) in a mixed solvent of ethanol (90 mL) and water (90 mL) was stirred at 55° C. for 5 hours, then 12 hours at ambient. The solution was adjusted to pH=6 with 6 N HCl carefully and subsequently stirred at room temperature for 2 hours. The precipitate was filtered off, washed with water. The collected white solid was dried under vacuum to give the product (9.2 g, 85%). m/z 267.1, 269.1 (M−H)−.

Workup

  1. custom12 hours
  2. stirringsubsequently stirred at room temperature for 2 hours
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customThe collected white solid was dried under vacuum

Sources & evidence

ORD record
ord-d002fe7a41f74adeae7cfac532980993
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Linked notes

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