m-Chloroperbenzoic acid → 2-Amino-4-methyl-5-(2-pyridylsulfinyl)thiazole

HRID 1656990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1656990
[NH2:1][C:2]1[S:3][C:4]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[C:5]([CH3:7])[N:6]=1.ClC1C=CC=C(C(OO)=[O:23])C=1>C(Cl)(Cl)Cl.ClCCl>[NH2:1][C:2]1[S:3][C:4]([S:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:23])=[C:5]([CH3:7])[N:6]=1

Komponenten

5

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 189547352-Amino-4-methyl-5-(2-pyridylthio)thiazole

Produkt 1

HCID 157291892-Amino-4-methyl-5-(2-pyridylsulfinyl)thiazoleAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A mixture of 2-amino-4-methyl-5-(2-pyridylthio)thiazole (1.7 g) and 3-chloroperbenzoic acid (1.8 g) in a mixture of chloroform (20 ml) and dichloromethane (50 ml) was stirred at 5° C. for 3.5 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-4-methyl-5-(2-pyridylsulfinyl)thiazole (0.95 g, yield: 52.2 %). mp: 190°-193° C. (dec.)

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-3d40e69cefd048dc94fa9772c97cb315
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05256675

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