Acetone → N-(1,3-dithiol-2-ylidene)-N-methyl-N-(2-phenyl-1-methoxycarbonylethyl)ammonium iodide

HRID 648905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 648905
CC(C)=O.[CH3:5][O:6][C:7](=[O:18])[C@H:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH:9][CH3:10].[I-:19].CS[C:22]1[S:26][CH:25]=[CH:24][S+:23]=1>O>[I-:19].[S:23]1[CH:24]=[CH:25][S:26][C:22]1=[N+:9]([CH3:10])[CH:8]([C:7]([O:6][CH3:5])=[O:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 7021804methyl (2S)-2-(methylamino)-3-phenylpropanoateHCID 19751531(2H-1,3-Dithiol-2-ylidene)(methyl)sulfanium iodide

Produkt 1

HCID 14127437N-(1,3-dithiol-2-ylidene)-N-methyl-N-(2-phenyl-1-methoxycarbonylethyl)ammonium iodideAusbeute 55,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To 100 ml of acetone, 2.2 g of N-methylphenylalanine methyl ester was dissolved, and 2.0 g of 2-methylthio-1,3-dithiolium iodide was gradually added thereto under stirring at room temperature. The mixture was stirred at room temperature for 1 hour, and then concentrated under reduced pressure. The residue was dissolved in water. The aqueous layer was washed with ethyl acetate, and then water was distilled off under reduced pressure, whereby 1.7 g (yield: 52%) of N-(1,3-dithiol-2-ylidene)-N-methyl-N-(2-phenyl-1-methoxycarbonylethyl)ammonium iodide (Compound No. 5) was obtained as oily substance.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. washThe aqueous layer was washed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2cbd11fe95fa4042b92d55b8baa71052
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04737494

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