Dimethylcarbamoyl Chloride → HCID 13753208, Verbindung

HRID 1732155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1732155
[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:16]=[CH:15][C:10]([O:11][CH2:12][CH2:13][OH:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>CN(C)C=O>[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:16]=[CH:15][C:10]([O:11][CH2:12][CH2:13][O:14][C:23](=[O:24])[N:22]([CH3:26])[CH3:21])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 13753176HCID 13753176, Verbindung

Produkt 1

HCID 13753208HCID 13753208, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A solution of 2.5 g of 2-[p-(p-fluorophenoxy)phenoxy]-ethanol in 25 ml of dimethylformamide is added dropwise during 20 minutes while stirring to a suspension of 0.5 g of sodium hydride (55% in oil) in 5 ml of dimethylformamide. The mixture is then allowed to stir at 40° C. for 4 hours, then treated dropwise with 1.18 g of dimethylcarbamoyl chloride and allowed to react at 40° C. for 16 hours. The cooled mixture is poured into 75 ml of ice/water and extracted three times with 50 ml of ethyl acetate each time. The extracts are washed three times with 50 ml of water each time, dried and evaporated. The residue is purified by chromatography on silica gel with n-hexane/ethyl acetate (85:15) to yield pure [2-[p-(p-fluorophenoxy)phenoxy]-ethyl]N,N-dimethylcarbamate; nD20 =1.5444.

Aufarbeitung

  1. customto react at 40° C. for 16 hours
  2. extractionextracted three times with 50 ml of ethyl acetate each time
  3. washThe extracts are washed three times with 50 ml of water each time
  4. customdried
  5. customevaporated
  6. customThe residue is purified by chromatography on silica gel with n-hexane/ethyl acetate (85:15)

Quellen und Nachweise

ORD-Eintrag
ord-c6163e5c6b234ee7b65d441e85bbb8d9
Quelldatensatz
uspto-grants-1986_11
Patentnummer
US04625048

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