Potassium Carbonate → 5-Benzyl-3-[2-(4-nitrophenyl)ethyl]imidazolidin-2,4-dione

HRID 483379

Reaction equation

HRID 483379 reaction equation
[CH2:1]([CH:8]1[NH:12][C:11](=[O:13])[NH:10][C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[N+:21]([C:24]1[CH:32]=[CH:31][C:27]([CH2:28][CH2:29]Br)=[CH:26][CH:25]=1)([O-:23])=[O:22]>CN(C=O)C>[CH2:1]([CH:8]1[NH:12][C:11](=[O:13])[N:10]([CH2:29][CH2:28][C:27]2[CH:26]=[CH:25][C:24]([N+:21]([O-:23])=[O:22])=[CH:32][CH:31]=2)[C:9]1=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 735655-(Phenylmethyl)-2,4-imidazolidinedioneHCID 792664-Nitrophenethyl bromide

Product 1

HCID 197525515-Benzyl-3-[2-(4-nitrophenyl)ethyl]imidazolidin-2,4-dioneYield 51.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of the product from step (a) (4.0 g) in DMF (10 ml) was added under N2 to a stirred suspension of anhy. K2CO3 (3.0 g) in DMF (10 ml), followed by the addition of a solution of p-nitrophenethyl bromide (4.9 g, Aldrich) in DMF (5 ml). After additions were complete, the mixture was stirred at room temperature for 17 hours, then at 40° C. for 48 hours. The mixture was poured into ice-water, stirred for 2 hours, and the resulting precipitate filtered off, washed with water, and triturated with ethanol to give the desired product as a pale yellow solid (3.7 g).

Workup

  1. waitat 40° C. for 48 hours
  2. stirringstirred for 2 hours
  3. filtrationthe resulting precipitate filtered off
  4. washwashed with water
  5. customtriturated with ethanol

Sources & evidence

ORD record
ord-3f7433f824dd48768850aa1cd6a5a23b
Source dataset
uspto-grants-1993_07
Patent number
US05225431

Linked notes

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