4-Fluoroaniline → Ethyl 1-(4-fluorophenyl)imidazole-5-carboxylate

HRID 2368477

Reaktionsgleichung

Reaktionsgleichung von HRID 2368477
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[CH:10]=O.C1(C)C(S([CH2:25][N+:26]#[C-:27])(=O)=O)=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Cl-].[Na+].O.C(O)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:10]([C:9]([O:13][CH2:14][CH3:15])=[O:12])=[CH:27][N:26]=[CH:25]2)=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 97314-FluoroanilineHCID 11430Potassium CarbonateHCID 70211Ethyl oxoacetateHCID 53627694Toluenesulfonylmethyl isocyanide

Produkt 1

HCID 55563221Ethyl 1-(4-fluorophenyl)imidazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A mixture of 4-fluoroaniline (2.8 g, 25.0 mmol), ethyl glyoxylate (50% solution, 5.14 g, 25.0 mmol), in toluene (30 mL) was refluxed overnight. The reaction was filtered and concentrated in vacuo. To the residue was added ethanol (30 mL), toluenesulfonylmethyl isocyanide (TOSMIC) (4.9 g, 25 mmol), and potassium carbonate (6.9 g, 50.0 mmol) and the mixture was stirred at room temperature for 1 h. Brine was added and mixture was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-60% EtOAc in hexanes) to afford ethyl 1-(4-fluorophenyl)-1H-imidazole-5-carboxylate (14a).

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. extractionmixture was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel (0-60% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-33e79decc8bd413a930d6697c18a1363
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703776B2

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