Potassium Iodide → Methyl 2-[4-(4-fluorophenoxy)phenoxy]-1-ethylcarbamate

HRID 1196642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1196642
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15].[F:17][C:18]1[CH:31]=[CH:30][C:21]([O:22][C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[CH:20][CH:19]=1>CN(C)C=O>[F:17][C:18]1[CH:31]=[CH:30][C:21]([O:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])=[CH:25][CH:24]=2)=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 251614Methyl (2-chloroethyl)carbamateHCID 129406244-(4-Fluorophenoxy)phenol

Produkt 1

HCID 57186014Methyl 2-[4-(4-fluorophenoxy)phenoxy]-1-ethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3.6 g of powdered potassium carbonate, 1.5 g of finely powdered potassium iodide and 27 g of methyl 2-chloroethylcarbamate are added to a solution of 2.6 g of 4-(4-fluorophenoxy)phenol in 120 ml of dimethyl formamide, and the reaction mixture is heated for 15 hours to 95° C. The cooled reaction mixture is poured into ice-water and extracted repeatedly with ether. The combined ether phases are washed with water, dried over sodium sulfate, and the solvent is completely removed by distillation. After filtration over silica gel, the crude product is recrystallised from diethyl ether/hexane to give methyl 2-[4-(4-fluorophenoxy)phenoxy]-1-ethylcarbamate with a melting point of 64°-66° C.

Aufarbeitung

  1. temperaturethe reaction mixture is heated for 15 hours to 95° C
  2. customThe cooled reaction mixture
  3. extractionextracted repeatedly with ether
  4. washThe combined ether phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is completely removed by distillation
  7. filtrationAfter filtration over silica gel
  8. customthe crude product is recrystallised from diethyl ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-a1cb456f8a5e48b19961922aa6daaf01
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05114968

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