Triethylamine → 4-(3-Ethoxy-2-hydroxypropoxy)phenylcarbamoylmethyl methyl sulfide

HRID 637531Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 637531
C(N(CC)CC)C.[CH2:8]([O:10][CH2:11][CH:12]([OH:22])[CH2:13][O:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1)[CH3:9].[CH3:23][S:24][CH2:25][C:26](Cl)=[O:27]>CN(C)C=O>[CH3:23][S:24][CH2:25][C:26](=[O:27])[NH:19][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH:12]([OH:22])[CH2:11][O:10][CH2:8][CH3:9])=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 107748571-(4-Aminophenoxy)-3-ethoxypropan-2-olHCID 111262562-(Methylsulfanyl)acetyl chloride

Produkt 1

HCID 133860734-(3-Ethoxy-2-hydroxypropoxy)phenylcarbamoylmethyl methyl sulfideAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Dissolved in 4 ml of dimethylformamide were 2.00 g of triethylamine and 2.11 g of 4-(3-ethoxy-2-hydroxypropoxy)aniline. To the solution was added 1.25 g of methylmercaptoacetyl chloride with ice-cooling and the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated and the residue was extracted with chloroform. The chloroform layer was washed with water and concentrated. The resulting residue was purified by silica gel column chromatography using a 1:5 ethanol-chloroform mixture, giving 2.85 g of 4-(3-ethoxy-2-hydroxypropoxy)phenylcarbamoylmethyl methyl sulfide in 95.3% yield.

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. extractionthe residue was extracted with chloroform
  4. washThe chloroform layer was washed with water
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8a22fcf10aea48389dc7633831772e6a
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04556737

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