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Methyl iodide → Methyl alpha-methylthio-alpha-(3-chloro-4-phthalimidophenyl)propionate

HRID 1277771
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1277771
[CH3:1][S:2][CH:3]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=[C:10]([Cl:25])[CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[CH3:28]I.[Cl-].[NH4+]>CN(C)C=O>[CH3:1][S:2][C:3]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=[C:10]([Cl:25])[CH:9]=1)([CH3:28])[C:4]([O:6][CH3:7])=[O:5]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 20556698HCID 20556698, Verbindung

Produkt 1

HCID 12819454Methyl alpha-methylthio-alpha-(3-chloro-4-phthalimidophenyl)propionateAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

Methyl α-methylthio(3-chloro-4-phthalimidophenyl)acetate was dissolved in 4.0 ml of dimethylformamide, and with ice cooling and stirring, 82 mg (65% content) of sodium hydride was added. The mixture was stirred for 10 minutes. With ice cooling, 0.2 ml of methyl iodide was added, but the deep red color did not vanish. Hence, 0.2 ml of methyl iodide was further added, and the mixture was stirred for about 1.5 hours at room temperature. The color of the solution became lighter, and turned orange. To the reaction solution was added 20 ml of an aqueous solution of ammonium chloride, and the mixture was extracted twice with 10 ml of methylene chloride. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residual orange oil was chromatographed on a column of Florisil using methylene chloride as an eluent to afford 0.453 g (68%) of methyl α-methylthio-α-(3-chloro-4-phthalimidophenyl)propionate as colorless crystals.

Aufarbeitung

  1. stirringThe mixture was stirred for 10 minutes
  2. stirringthe mixture was stirred for about 1.5 hours at room temperature
  3. extractionthe mixture was extracted twice with 10 ml of methylene chloride
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residual orange oil was chromatographed on a column of Florisil

Quellen und Nachweise

ORD-Eintrag
ord-d811d55a6302408db510748204789699
Quelldatensatz
uspto-grants-1981_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04278802

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