Water → ethyl 1-(4-chlorobenzyl)-1H-imidazole-2-carboxylate

HRID 83658Notes

Reaction equation

HRID 83658 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([O:8][CH2:9][CH3:10])=[O:7].[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:1]2[CH:5]=[CH:4][N:3]=[C:2]2[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 10340Sodium CarbonateHCID 549404ethyl 1H-imidazole-2-carboxylate

Product 1

HCID 68379775ethyl 1-(4-chlorobenzyl)-1H-imidazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 1H-imidazole-2-carboxylate (4 g, 28.5 mmol), p-chlorobenzylchloride (4.38 mL, 34.3 mmol), and sodium carbonate (3.63 g, 34.3 mmol), was dissolved in DMF (8 mL). The solution was stirred at rt for 24 h, at which time water was added and material was extracted with EtOAc. The organic phase was collected, dried over magnesium sulfate, and decanted. Purification accomplished via silica gel flash chromatography (150 g silica, 10% EtOAc/Hexanes to 80% EtOAc/Hexanes.) The title compound was obtained as a clear, yellow-tinted oil. (Yield: 7.28 g, 27.5 mmol, 96%) 1H NMR (400 MHz, CDCl3) 7.25, 7.15, 7.10-7.00, 5.55, 4.34, 1.36

Workup

  1. additionwas added
  2. extractionmaterial was extracted with EtOAc
  3. customThe organic phase was collected
  4. dry with materialdried over magnesium sulfate
  5. customdecanted
  6. customPurification
  7. customwas obtained as a clear, yellow-tinted oil

Sources & evidence

ORD record
ord-ae834a5e0c3947ca8859df7634d1354e
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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