Hydantoin → 3-(4-Formylbenzyl)hydantoin

HRID 591754Notes

Reaction equation

HRID 591754 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[H-].[Na+].Br[CH2:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.[NH4+].[Cl-]>CN(C=O)C>[O:3]=[C:2]1[NH:1][CH2:7][C:5](=[O:6])[N:4]1[CH2:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 10006HydantoinHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 112064214-(Bromomethyl)benzaldehyde

Product 1

HCID 187585643-(4-Formylbenzyl)hydantoin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Hydantoin (0.80 g, 8.00 mmol) was dissolved in DMF (10 mL) and cooled to 0° C. Sodium hydride (60% in mineral oil, 88 mg, 2.20 mmol) was added. The mixture was stirred at room temperature for 3 hours. 4-(Bromomethyl)benzaldehyde (0.40 g, 2.00 mmol) was added. The mixture was stirred at room temperature for 2.5 days. Saturated aqueous NH4Cl (1 mL) was added. The mixture was concentrated to dryness. Water (10 mL) was added, extracted with dichloromethane, and the organic phase was dried over anhydrous Na2SO4. Solvent was removed and the crude compound was purified by column chromatography (silica gel 230-400 mesh; 5% methanol in CH2Cl2 as eluent) to give 4-(2,5-dioxo-imidazolidin-1-ylmethyl)-benzaldehyde as a white solid. Yield: 0.28 g (64%).

Workup

  1. stirringThe mixture was stirred at room temperature for 2.5 days
  2. concentrationThe mixture was concentrated to dryness
  3. additionWater (10 mL) was added
  4. extractionextracted with dichloromethane
  5. dry with materialthe organic phase was dried over anhydrous Na2SO4
  6. customSolvent was removed
  7. customthe crude compound was purified by column chromatography (silica gel 230-400 mesh; 5% methanol in CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-6bcfb8c7fc784a0ea38b62b9e57259a8
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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