Sodium Thiosulfate → ethyl 1-(4-fluorophenyl)-2-iodo-1H-imidazole-5-carboxylate

HRID 2368498Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2368498
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[CH:9]2)=[CH:4][CH:3]=1.[I:18]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9]2[I:18])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 55563221Ethyl 1-(4-fluorophenyl)imidazole-5-carboxylate

Produkt 1

HCID 71117744ethyl 1-(4-fluorophenyl)-2-iodo-1H-imidazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of ethyl 1-(4-fluorophenyl)-1H-imidazole-5-carboxylate (14) (5 g, 21.4 mmol), N-iodosuccinimide (12 g, 53.4 mmol), and THF (100 mL) was refluxed overnight. A solution of saturated sodium thiosulfate was added and the reaction 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 (0-100% EtOAc in hexanes) to give ethyl 1-(4-fluorophenyl)-2-iodo-1H-imidazole-5-carboxylate (38).

Aufarbeitung

  1. extractionthe reaction was extracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (0-100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a60408fff8234c38825626e3cfffd07a
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703776B2

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