Benzyl Bromide → HCID 19752533, compound

HRID 483374Notes

Reaction equation

HRID 483374 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][N:9]2[C:13](=[O:14])[CH2:12][NH:11][C:10]2=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[CH2:24]([N:11]1[CH2:12][C:13](=[O:14])[N:9]([CH2:8][C:7]2[CH:16]=[CH:17][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:10]1=[O:15])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 107522073-(4-Nitrobenzyl)imidazolidine-2,4-dione

Product 1

HCID 19752533HCID 19752533, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of the product from step (a) (5.9 g) in DMF (15 ml) was added under N2 to a stirred suspension of anhy. K2CO3 (3.5 g) in DMF (15 ml), followed by the addition of benzyl bromide (4.3 g, Aldrich). After additions were complete, the mixture was stirred at room temperature for 16 hours, then poured into ice-water and extracted with ethyl acetate (×3). The combined extracts were washed with brine, dried over MgSO4 and evaporated to give a yellow oil which was flash chromatographed through a silica column using ethyl acetate to give the desired product as a yellow oil (7.0 g).

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. washThe combined extracts were washed with 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-f3376990fd3f4155ab32bbff1775b71d
Source dataset
uspto-grants-1993_07
Patent number
US05225431

Reaction notes

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