Potassium Carbonate → (1-Naphthalen-2-ylmethyl-2,5-dioxo-imidazolidin-4-yl)-acetic acid methyl ester

HRID 1985182Notes

Reaction equation

HRID 1985182 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH:5]1[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6]1.Br[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1.[O-]S([O-])(=O)=O.[Mg+2].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH:5]1[C:9](=[O:10])[N:8]([CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[C:7](=[O:11])[NH:6]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 703202-BromomethylnaphthaleneHCID 5296047Methyl (2,5-dioxoimidazolidin-4-yl)acetate

Product 1

HCID 57719019(1-Naphthalen-2-ylmethyl-2,5-dioxo-imidazolidin-4-yl)-acetic acid methyl esterYield 53.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2,5-dioxo-imidazolidin-4-yl)-acetic acid methyl ester (6.48 g, 37.6 mmol) in DMF (250 mL) is treated with 2-(bromomethyl)-napthalene (9.15 g, 41.4 mmol), MgSO4 (4.53 g, 37.6 mmol) and then K2CO3 (15.61 g, 0.113 mol) at 0° C. The resultant mixture is warmed to room temperature and stirred under N2 for 16 hours. The reaction mixture is filtered, and then aqueous 1N HCl (300 mL) is added to the filtrate. The filtrate is extracted with Et2O and the organic layer dried. The solvent is removed to give a crude oil which is purified by flash chromatography using 2:1 hexanes:acetone to afford 6.27 g of (1-naphthalen-2-ylmethyl-2,5-dioxo-imidazolidin-4-yl)-acetic acid methyl ester (53%). Rf=0.32 (1:1 hexanes:acetone). 1H NMR.

Workup

  1. customat 0° C
  2. filtrationThe reaction mixture is filtered
  3. additionaqueous 1N HCl (300 mL) is added to the filtrate
  4. extractionThe filtrate is extracted with Et2O
  5. customthe organic layer dried
  6. customThe solvent is removed
  7. customto give a crude oil which
  8. customis purified by flash chromatography

Sources & evidence

ORD record
ord-814ff19bf21f4e2691be4cef07e5fb40
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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