m-Chloroperbenzoic acid → 2-Amino-5-(2-pyridylsulfinyl)thiazole

HRID 1656959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1656959
Cl.Cl.[NH2:3][C:4]1[S:5][C:6]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:7][N:8]=1.ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)(Cl)Cl>[NH2:3][C:4]1[S:5][C:6]([S:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[O:24])=[CH:7][N:8]=1

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 189547342-Amino-5-(2-pyridylthio)thiazole dihydrochloride

Produkt 1

HCID 101307512-Amino-5-(2-pyridylsulfinyl)thiazoleAusbeute 106,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a solution of 2-amino-5-(2-pyridylthio)thiazole dihydrochloride (4.0 g) in chloroform (100 ml) was dropwise added the solution of 3-chloroperbenzoic acid (5.0 g) in chloroform (100 ml) at 5° C. with stirring. The mixture was stirred at 5° C. for 1.5 hours. The reaction mixture was washed with aqueous sodium bicarbonate and dried over magnesium sulfate. The solvent was concentrated under reduced pressure to give solid. The solid was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 100 g) and eluted with a mixture of chloroform and methanol (10:1). The fractions containing the objective compound were combined and concentrated under reduced pressure to give 2-amino-5-(2-pyridylsulfinyl)thiazole (3.4 g, yield: 78.9%). mp: 200°-202° C. (dec.) IR (Nujol): 3300, 3150, 1630, 1575, 1270, 1225 cm-1

Aufarbeitung

  1. stirringThe mixture was stirred at 5° C. for 1.5 hours
  2. washThe reaction mixture was washed with aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customto give solid
  6. washeluted with a mixture of chloroform and methanol (10:1)
  7. additionThe fractions containing the objective compound
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4b77eb8c7a944b07871a708dcf9317ea
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05256675

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