Potassium Carbonate → 4-(N,N-diethylaminopropoxy)butyranilide

HRID 503665

Reaktionsgleichung

Reaktionsgleichung von HRID 503665
S(Cl)(C)(=O)=O.[CH2:6]([N:8]([CH:11](O)[CH2:12][CH3:13])[CH2:9][CH3:10])[CH3:7].[C:15]([NH:20][C:21]1[CH:26]=[CH:25][C:24](O)=[CH:23][CH:22]=1)(=[O:19])[CH2:16][CH2:17][CH3:18].C([O-])([O-])=[O:29].[K+].[K+]>C(Cl)Cl.CN(C=O)C>[CH2:6]([N:8]([CH2:11][CH2:12][CH2:13][O:29][CH2:18][CH2:17][CH2:16][C:15]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[CH2:9][CH3:10])[CH3:7]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 668744'-HydroxybutyranilideHCID 5256659Diethylamino-propanol

Produkt 1

HCID 684301664-(N,N-diethylaminopropoxy)butyranilideAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Mesyl Chloride (6.0 mmol) was added dropwise at 0° C. to a stirred solution of N,N-diethylaminopropanol (6.0 mmol), TEA (6.0 mmol) in anhydrous DCM (6 mL), and the mixture was stirred at the same temperature for 10 min, and at room temperature for additional 1 h. After the removal of the solvent in vacuo, the solid residue was mixed with 4-butyramidophenol (5.0 mmol), and K2CO3 (10 mmol) in anhydrous DMF (10 mL), following general procedure B. The crude product is purified using silica gel column chromatography 5% MeOH/DCM as eluent to yield 4-(N,N-diethylaminopropoxy)butyranilide (1.4 g).

Aufarbeitung

  1. waitat room temperature for additional 1 h
  2. customAfter the removal of the solvent in vacuo
  3. customThe crude product is purified

Quellen und Nachweise

ORD-Eintrag
ord-21acd754eb5d4c3d8cff4ba5df20afc0
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776919B2

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