m-Chloroperbenzoic acid → 2-Amino-5-(5-trifluoromethylpyridin-2-ylsulfinyl)thiazole

HRID 1657002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1657002
[NH2:1][C:2]1[S:3][C:4]([S:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=2)=[CH:5][N:6]=1.ClC1C=CC=C(C(OO)=[O:26])C=1>ClCCl>[NH2:1][C:2]1[S:3][C:4]([S:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=2)=[O:26])=[CH:5][N:6]=1

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 157292002-Amino-5-(5-trifluoromethylpyridin-2-ylthio)thiazole

Produkt 1

HCID 157292052-Amino-5-(5-trifluoromethylpyridin-2-ylsulfinyl)thiazoleAusbeute 81,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-5-(5-trifluoromethylpyridin-2-ylthio)thiazole (0.6 g) in dichloromethane (20 ml) was added portionwise 3-chloroperbenzoic acid (0.6 g) at 5° C. with stirring. The mixture was stirred at 5° C. for 3 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: 30 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-(5-trifluoromethylpyridin-2-ylsulfinyl)thiazole (0.52 g, yield: 81.9%). mp: 144°-145° C.

Aufarbeitung

  1. stirringThe mixture was stirred at 5° C. for 3 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-faaa2f8cb7da41e4a467e7ae572ff0cb
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05256675

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