Potassium Carbonate → Ethyl 3-[1-(4-methyl-2-nitrophenyl)-1H-imidazol-2-yl]-propanoate

HRID 576858Notes

Reaction equation

HRID 576858 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>C(OCC)C>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 1362874-Fluoro-3-nitrotolueneHCID 22259341Ethyl 3-(1H-imidazol-2-YL)propanoate

Product 1

HCID 59198588Ethyl 3-[1-(4-methyl-2-nitrophenyl)-1H-imidazol-2-yl]-propanoateYield 92.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Fluoro-4-methyl-2-nitrobenzene 239 mg, ethyl 3-(1H-imidazol-2-yl)propanoate 252 mg, potassium carbonate 415 mg and N,N-dimethylacetamide 10 mL were stirred at 100° C. for 11.5 hours, and then at 130° C., for 6 hours. The reaction liquid was diluted with diethyl ether, washed with water and saturated brine by the order stated, and dried over magnesium sulfate. Distilling the solvent off under reduced pressure, the residue was subjected to silica gel chromatography (ethyl acetate) to provide 422 mg of the title compound.

Workup

  1. customThe reaction liquid
  2. washwashed with water and saturated brine by the order
  3. dry with materialdried over magnesium sulfate
  4. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-f4b7ec95e07e4c0a87150dc9f8adfe31
Source dataset
uspto-grants-2015_05
Patent number
US09040536B2

Reaction notes

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