Urea → 2-(3-bromo-2-oxopropyl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 2402097Notes

Reaction equation

HRID 2402097 reaction equation
[C:1]1(=[O:15])[N:5]([CH2:6][C:7](=[O:9])[CH3:8])[C:4](=[O:10])[C:3]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:2]12.NC(N)=O.[Br:20]Br>CO>[Br:20][CH2:8][C:7](=[O:9])[CH2:6][N:5]1[C:4](=[O:10])[C:3]2[C:2](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:1]1=[O:15]

Participants

5

Reactant 3

HCID 1176UreaHCID 24408BromineHCID 235046Phthalimidoacetone

Product 1

HCID 2220372-(3-bromo-2-oxopropyl)-2,3-dihydro-1H-isoindole-1,3-dioneYield 3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of phthalimidoacetone (4.04 g, 19.9 mmol) in methanol (100 mL) was added urea (1.19 g, 19.9 mmol) and bromine (3.18 g, 19.9 mmol) and the resulting solution was stirred at room temperature overnight. The reaction was concentrated in vacuo and the residue taken up in DCM (150 mL) and water (50 mL). The layers were separated and the organic layer was dried, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (EA/hexanes=0/100→50/50) to give 159 mg (3% yield) of the title compound. 1H NMR (300 MHz, CDCl3) δ: 7.90-7.86 (m, 2H), 7.79-7.73 (m, 2H), 4.78 (s, 2H), 4.01 (s, 2H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe layers were separated
  3. customthe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (EA/hexanes=0/100→50/50)

Sources & evidence

ORD record
ord-9f1bacd16dbc4af58d3ae9d963a7a648
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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