Imidazole → HCID 18695417, compound

HRID 1870218Notes

Reaction equation

HRID 1870218 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][NH:6][C:7]1[CH:12]=[C:11](F)[C:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=2)=[CH:9][C:8]=1[N+:26]([O-:28])=[O:27])[CH3:2].[NH:30]1[CH:34]=[CH:33][N:32]=[CH:31]1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([N:30]2[CH:34]=[CH:33][N:32]=[CH:31]2)[C:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=2)=[CH:9][C:8]=1[N+:26]([O-:28])=[O:27])[CH3:2]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 18695430HCID 18695430, compound

Product 1

HCID 18695417HCID 18695417, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.78 g (4.39 mmol) of N-[4-(4-ethoxycarbonylphenoxy)-5-fluoro-2-nitrophenyl]glycine ethyl ester, 896 mg of imidazole and 20 ml of DMF was stirred with heating on an oil bath of 70° C. for 12 hours. After cooling, the reaction mixture was concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate. The resulting solution was washed successively with water and brine, dried over anhydrous sodium sulfate and then, concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (developing solvent: chloroform+0 to 1% methanol) to give 1.49 g (75%) of N-[4-(4-ethoxycarbonylphenoxy)-5-(1H-imidazol-1-yl)-2-nitrophenyl]glycine ethyl ester.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in ethyl acetate
  4. washThe resulting solution was washed successively with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by chromatography on a silica gel column (developing solvent: chloroform+0 to 1% methanol)

Sources & evidence

ORD record
ord-f346785e5ae54c388f1c666f92d78fbe
Source dataset
uspto-grants-2000_08
Patent number
US06096743

Reaction notes

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