Hydrochloric Acid → HCID 18667552, Verbindung

HRID 1059881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1059881
[NH2:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=2)=[C:5]([CH3:7])[N:6]=1.CS[C:17]1[S:18][CH2:19][CH2:20][N:21]=1.Cl.C(=O)([O-])O.[Na+]>COC(O)C.O1CCOCC1>[CH3:7][C:5]1[N:6]=[C:2]([NH:1][C:17]2[S:18][CH2:19][CH2:20][N:21]=2)[S:3][C:4]=1[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 883244,5-Dihydro-2-(methylthio)thiazoleHCID 516892Sodium BicarbonateHCID 186309852-Amino-4-methyl-5-(4-methylpyridin-2-yl)-thiazole

Produkt 1

HCID 18667552HCID 18667552, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 312751,4-DioxaneLösungsmittelHCID 30156371-MethoxyethanolLösungsmittel

Versuchsvorschrift

To a suspension of 2-amino-4-methyl-5-(4-methylpyridin-2-yl)-thiazole and 2-(methylthio)-2-thiazoline (127 mg) in methoxyethanol (2 ml) was added a solution of hydrogen chloride in 1,4-dioxane (4N, 0.23 ml). The mixture was refluxed for 20 hours, poured into a saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate twice. The combined organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 25 g, 5% methanol in dichloromethane) and recrystallized from chloroform (1 ml)-diisopropyl ether (3 ml) to give 2-(4-methyl-5-(4-methylpyridin-2-yl)thiazol-2-ylamino)-2-thiazoline (110 mg).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 20 hours
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel 25 g, 5% methanol in dichloromethane)
  7. customrecrystallized from chloroform (1 ml)-diisopropyl ether (3 ml)

Quellen und Nachweise

ORD-Eintrag
ord-e7ef9cd76e19482bb0ebc62b6c60a001
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521643B1

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