Potassium Carbonate → HCID 18928109, compound

HRID 1599429Notes

Reaction equation

HRID 1599429 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][C:13]1[N:14]=[CH:15][NH:16][C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:21]([O:20][C:18]([C:17]1[N:16]=[CH:15][N:14]([C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[C:13]=1[CH3:12])=[O:19])[CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 679672,4-DifluoronitrobenzeneHCID 178470400HCID 178470400, compound

Product 1

HCID 18928109HCID 18928109, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2,4-difluoronitrobenzene (36.6 g, 230 mmol), ethyl 4-methyl-5-imidazolecarboxylate (35.6 g, 231 mmol), potassium carbonate (36.5 g, 264.4 mmol) and acetonitrile (250 ml) was stirred at 25° C. for 96 h. The reaction mixture was filtered and the solvent removed under reduced pressure. The residue was submitted to flash chromatography on silica gel 60 eluting with toluene graduated to toluene/ethyl acetate (1:1) to give 30.5 g (65%) of 4-ethoxycarbonyl-5-methyl-1-(2-nitro-5-fluorophenyl)-1H-imidazole.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-698d7379085c4a26a2d83f8162df760c
Source dataset
uspto-grants-1998_04
Patent number
US05741785

Reaction notes

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