Imidazole → methyl 2-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-acetate

HRID 12301Notes

Reaction equation

HRID 12301 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(N(CC)CC)C.Br[CH:14]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:15]([O:17][CH3:18])=[O:16].O>CN(C=O)C>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([CH:14]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[C:15]([O:17][CH3:18])=[O:16])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 8471TriethylamineHCID 10777987Methyl 2-bromo-2-(4-chlorophenyl)acetate

Product 1

HCID 23092022methyl 2-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-acetateYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of imidazole (170 mg) and triethylamine (350 ml) in DMF (1 ml), a solution of methyl 2-bromo-2-(4-chlorophenyl)-acetate (657 mg) in DMF (3 ml) was added. After stirring for an overnight, water was added to the reaction liquid, followed by extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate. The reaction liquid was condensed under reduced pressure and the resulting residue was purified on silica gel column chromatography (methanol/chloroform=1/10) to provide methyl 2-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-acetate (400 mg) as a yellow oily substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washwashing with saturated brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. customThe reaction liquid
  5. customcondensed under reduced pressure
  6. customthe resulting residue was purified on silica gel column chromatography (methanol/chloroform=1/10)

Sources & evidence

ORD record
ord-c5bb6ebc07cd49ad9ab13e25aeb3b07a
Source dataset
uspto-grants-2010_06
Patent number
US07727998B2

Reaction notes

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