Dimethylformamide → HCID 22966909, Verbindung

HRID 2306000Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2306000
[N:1]([CH2:4][CH2:5][CH3:6])=[C:2]=[S:3].CN(C)C=O.[NH2:12][C:13]1[S:14][CH:15]=[CH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19]>O>[CH2:4]([NH:1][C:2](=[S:3])[NH:12][C:13]1[S:14][CH:15]=[CH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19])[CH2:5][CH3:6]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 69403Propyl IsothiocyanateHCID 78381Methyl 2-amino-3-thenoate

Produkt 1

HCID 22966909HCID 22966909, VerbindungAusbeute 40,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
132.5 °C

Versuchsvorschrift

In a sulfonation flask, 2.02 g (0.02 mol) of 1-isothiocynatopropane are added dropwise to 30 ml dimethylformamide and 3.0 g (0.019 mol) of methyl 2-aminothiophene-3-carboxylate. The reaction mixture is then stirred at 130-135° C. for 12 hours and after cooling added to 120 ml of water. The resulting mixture is then extracted three times with ethylacetate and the separated organic phase dried over sodium sulfate. The solvent is then removed in a water-jet vacuum, giving the crude product as a dark oil, which is purified by column chromatography over silica gel (eluant: tert.butylmethylether/hexane=2:3). 2.0 g of methyl 2-(3-propylthioureido)thiophene-3-carboxylate are obtained in the form of a yellow powder having a melting point of 122-124° C.

Aufarbeitung

  1. temperatureafter cooling
  2. extractionThe resulting mixture is then extracted three times with ethylacetate
  3. dry with materialthe separated organic phase dried over sodium sulfate
  4. customThe solvent is then removed in a water-jet vacuum
  5. customgiving the crude product as a dark oil, which
  6. customis purified by column chromatography over silica gel (eluant: tert.butylmethylether/hexane=2:3)

Quellen und Nachweise

ORD-Eintrag
ord-301c832c24364a8789e8b94b397fcabb
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06441169B1

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