1,2-Dibromoethane → 1-Benzyloxy-3-(4,4-dimethoxy-butyl)-imidazolidin-2-one

HRID 251005Notes

Reaction equation

HRID 251005 reaction equation
[CH3:1][O:2][CH:3]([O:19][CH3:20])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:18])[NH:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Br[CH2:24][CH2:25]Br>CN(C=O)C.CCOC(C)=O>[CH2:11]([O:10][N:9]1[CH2:25][CH2:24][N:7]([CH2:6][CH2:5][CH2:4][CH:3]([O:19][CH3:20])[O:2][CH3:1])[C:8]1=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydride2×HCID 865947613-(4,4-Dimethoxy-butyl)-1-(benzyloxy)-urea

Product 1

HCID 672725081-Benzyloxy-3-(4,4-dimethoxy-butyl)-imidazolidin-2-oneYield 36%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(4,4-dimethoxy-butyl)-1-(benzyloxy)-urea (4.14 g, 14.7 mmol) in DMF (40 mL) was added NaH (60 wt % in mineral oil, 0.659 g, 16.5 mmol). After 30 minutes, 1,2-dibromoethane (1.30 mL, 15.1 mmol) was added and the mixture was stirred for an additional 40 minutes. An additional amount of NaH (60 wt % in mineral oil, 0.636 g, 15.9 mmol) was added and the mixture was stirred at room temperature for 3 hours. The mixture was diluted with EtOAc (150 mL), washed with brine (5×25 mL), dried (MgSO4), and concentrated. Purification of the crude material by column chromatography on silica gel (1:1 hexanes-EtOAc) provided 1.61 g (36%) of 1-Benzyloxy-3-(4,4-dimethoxy-butyl)-imidazolidin-2-one as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. washwashed with brine (5×25 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification of the crude material by column chromatography on silica gel (1:1 hexanes-EtOAc)

Sources & evidence

ORD record
ord-c5923d31ea3c4be8a14082fa983f2376
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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