Potassium Carbonate → HCID 19752534, compound

HRID 483380Notes

Reaction equation

HRID 483380 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][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:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1)([O-:23])=[O:22]>CN(C=O)C>[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][N:10]([CH2:28][C:27]2[CH:30]=[CH:31][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][CH:26]=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 660114-Nitrobenzyl bromideHCID 2319592,4-IMIDAZOLIDINEDIONE, 3-(PHENYLMETHYL)-

Product 1

HCID 19752534HCID 19752534, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 3-benzylimidazolidin-2,4-dione (5.7 g, JACS 1965, 3414) in DMF (10 ml) was added under N2 to a stirred suspension of anhy. K2CO3 (4.1 g) in DMF (10 ml), followed by the addition of a solution of p-nitrobenzyl bromide (6.45 g, Aldrich) in DMF (10 ml). After additions were complete, the mixture was stirred at room temperature for 72 hours, then poured into ice-water and extracted with ethyl acetate (×3). The combined extracts were washed with water (×2) and brine, dried over MgSO4 and evaporated to give a yellow oil which was flash chromatographed through a silica column using chloroform to give the desired product as a pale yellow solid (7.9 g).

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. washThe combined extracts were washed with water (×2) and brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customto give a yellow oil which
  6. customchromatographed through a silica column

Sources & evidence

ORD record
ord-520fd264b74f4c0187c9e00f1810f209
Source dataset
uspto-grants-1993_07
Patent number
US05225431

Reaction notes

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