Sodium Iodide → HCID 178469080, Verbindung

HRID 744064

Reaktionsgleichung

Reaktionsgleichung von HRID 744064
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.Cl.Cl[CH2:15][CH2:16][C:17]1[N:18]=[CH:19][NH:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[CH2:9]([O:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:15][CH2:16][C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)=[CH:12][CH:11]=1)=[O:7])[CH3:10]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 1784785704-(2-chloroethyl)-1H-imidazole hydrochloride

Produkt 1

HCID 178469080HCID 178469080, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.49 g (9 mmol) of ethyl 4-hydroxybenzoate, 251 mg (1.5 mmol) of 4-(2-chloroethyl)-1H-imidazole hydrochloride, 500 g (3.6 mmol) of potassium carbonate and sodium iodide (catalyst) are stirred at 80° C. for 4 days in 5 ml of dimethylformamide. The reaction mixture is cooled and then filtered. The filtrate is evaporated under reduced pressure to give an oily residue. The excess ethyl 4-hydroxybenzoate is extracted with ether at pH=1. The aqueous solution is evaporated under reduced pressure to give the title compound. The latter is purified by preparative high performance chromatography and converted to the oxalate which, after crystallization from an isopropanol/ether mixture, melts at 160°-164° C.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. customThe filtrate is evaporated under reduced pressure
  4. customto give an oily residue
  5. extractionThe excess ethyl 4-hydroxybenzoate is extracted with ether at pH=1
  6. customThe aqueous solution is evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-37b947fe38e748aca21ed87b467e4b05
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05559113

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