p-Xylyl bromide → HCID 57718991, compound

HRID 1985176Notes

Reaction equation

HRID 1985176 reaction equation
[O:1]=[C:2]1[NH:6][CH:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[C:4](=[O:12])[NH:3]1.[CH3:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.[O-]S([O-])(=O)=O.[Mg+2].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:11][O:10][C:8](=[O:9])[CH2:7][CH:5]1[C:4](=[O:12])[N:3]([CH2:13][C:14]2[CH:21]=[CH:20][C:17]([CH3:18])=[CH:16][CH:15]=2)[C:2](=[O:1])[NH:6]1

Participants

6

Reactant 4

HCID 7721p-Xylyl bromideHCID 11430Potassium CarbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5296047Methyl (2,5-dioxoimidazolidin-4-yl)acetate

Product 1

HCID 57718991HCID 57718991, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2,5-dioxo-imidazolidin-4-yl)-acetic acid, methyl ester (2.35 g, 13.7 mmol) in DMF (100 mL) is treated with p-methyl benzyl bromide (2.90 g, 15.7 mmol), MgSO4 (3.30 g, 27.4 mmol) and then K2CO3 (3.77 g, 27.3 mmol). The resultant mixture is stirred under N2 in an ice bath for 30 minutes and then warmed to room temperature for 16 h. The reaction mixture is then filtered, and then aqueous 1N HCl (150 mL) is added to the filtrate. The filtrate is extracted with EtOAc and the organic layer dried. The solvent is removed to give 4.11 g crude product which is purified by flash chromatography using 100% CH2Cl2 then 97.5:2.5 CH2Cl2:MeOH to give 3.67 g (97%) [1-(4-methyl-benzyl)-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester. 1H NMR. MS (ES+) Calc'd for C14H17N2O4 (M+1) 277. Found m/z 277 (100%).

Workup

  1. filtrationThe reaction mixture is then filtered
  2. additionaqueous 1N HCl (150 mL) is added to the filtrate
  3. extractionThe filtrate is extracted with EtOAc
  4. customthe organic layer dried
  5. customThe solvent is removed
  6. customto give 4.11 g crude product which
  7. customis purified by flash chromatography

Sources & evidence

ORD record
ord-527ef5b1b0364256adb696464defa5be
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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