Water → 1-Benzylimidazolidin-2-one

HRID 1811045

Reaction equation

HRID 1811045 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].[H-].[Na+].Br[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>CN(C=O)C>[CH2:10]([N:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 84532-ImidazolidinoneHCID 24758Sodium hydride

Product 1

HCID 2314031-Benzylimidazolidin-2-oneYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step 1 A solution of imidazolidin-2-one (500 mg, 5.81 mmol) in DMF (30 mL) was stirred on ice and treated with sodium hydride, 60% oil dispersion (264 mg, 6.60 mmol). The mixture was stirred at rt for 50 min, then was treated with (bromomethyl)benzene (0.691 mL, 5.81 mmol). After 2 h, the mixture was poured into water and extracted three times with EtOAc. The combined organic layers were dried and concentrated, and the residue was purified by column chromatography (eluting with EtOAc) to provide 1-benzylimidazolidin-2-one as a white solid (160 mg, 16%). 1H NMR (400 MHz, chloroform-d) δ 7.22-7.39 (5 H, m), 4.53 (1 H, br. s.), 4.37 (2 H, s), 3.25-3.46 (4 H, m).

Workup

  1. waitAfter 2 h
  2. extractionextracted three times with EtOAc
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography (eluting with EtOAc)

Sources & evidence

ORD record
ord-54add59c9343403ca4fe325f0276d458
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Linked notes

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