Pyridine → HCID 13805985, Verbindung

HRID 2292022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2292022
[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](Cl)=[O:6].[CH3:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]([CH3:18])=[CH:13][S:12]1.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[CH3:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]([CH3:18])=[C:13]([CH:22]2[CH:23]=[CH:24][N:19]([C:5]([O:4][CH2:3][C:2]([Cl:9])([Cl:8])[Cl:1])=[O:6])[CH:20]=[CH:21]2)[S:12]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 13805967HCID 13805967, Verbindung

Produkt 1

HCID 13805985HCID 13805985, VerbindungAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2,2,2-Trichloroethylchloroformate (1.68 ml) was added dropwise to a solution of 2,5-dimethyl-2H-1,4-thiazin-3(4H)-one (1.43 g) and pyridine (1.6 ml) in acetonitrile (50 ml) under ice-cooling, and the solution was stirred for 30 minutes at 0° C. The mixture was further stirred at ambient temperature for 2 hours. The solvent was removed under reduced pressure. The residue was extracted with chloroform, was washed with 2N hydrochloric acid and successively with water and was dried over magnesium sulfate. The solvent was removed and the residue was chromatographed on silica gel (Wakogel C-200) column, using ethyl acetate-n-hexane (=1:1) as an eluant. The eluate was washed with ether to give the titled compound (1.68 g, yield 42%) as pale yellow crystals.

Aufarbeitung

  1. temperaturecooling
  2. stirringThe mixture was further stirred at ambient temperature for 2 hours
  3. customThe solvent was removed under reduced pressure
  4. extractionThe residue was extracted with chloroform
  5. washwas washed with 2N hydrochloric acid and successively with water
  6. dry with materialwas dried over magnesium sulfate
  7. customThe solvent was removed
  8. customthe residue was chromatographed on silica gel (Wakogel C-200) column
  9. washThe eluate was washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-a4f5087f3de3449b86ed1e5c254dbe55
Quelldatensatz
uspto-grants-1989_01
Patentnummer
US04800201

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