Phosphorus trichloride → HCID 18350679, Verbindung

HRID 430511

Reaktionsgleichung

Reaktionsgleichung von HRID 430511
[NH2:1][C:2]1[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:9]([NH:12][C:13]1[CH:17]=[CH:16][S:15][C:14]=1[C:18](O)=[O:19])(=O)[CH3:10].P(Cl)(Cl)Cl>N1C=CC=CC=1>[CH3:10][C:9]1[N:1]([C:2]2[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=2)[C:18](=[O:19])[C:14]2[S:15][CH:16]=[CH:17][C:13]=2[N:12]=1

Komponenten

5

Edukt 3

HCID 24387Phosphorus trichlorideHCID 805282-Chloro-3-pyridylamineHCID 28075793-Acetamidothiophene-2-carboxylic acid

Produkt 1

HCID 18350679HCID 18350679, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

To a mixture of pyridine (4 mL), 3-amino-2-chloropyridine (0.514 g, 4 mmol), and 3-acetamidothiophene-2-carboxylic acid (0.370 g, 4 mmol) was added phosphorus trichloride (0.02 mL, 2.3 mmol). The reaction was heated to 105° C. for 3 hours, cooled to ambient temperature and partitioned between ethyl acetate and water. Phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic phase was washed with water and brine, dried over sodium sulfate and concentrated to a greenish brown oil. This residue was flash chromatographed on silica gel (20×120 mm) eluting with 20-40% ethyl acetate/hexane to afford 0.350 g (63%) of 2-methyl-3-(2-chloropyrid-3-yl)-3H-thieno[3,2-d]pyrimidin-4-one as a yellow foam.

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. custompartitioned between ethyl acetate and water
  3. customPhases were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic phase was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to a greenish brown oil
  8. customchromatographed on silica gel (20×120 mm)
  9. washeluting with 20-40% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-2d0269e9bbed4ddebd146f92e46f6348
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06323208B1

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