m-Chloroperbenzoic acid → 4H-1,2,4-Triazole, 4-methyl-3-(methylsulfinyl)-5-(2-thienyl)-

HRID 1199383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1199383
[CH3:1][N:2]1[C:6]([S:7][CH3:8])=[N:5][N:4]=[C:3]1[C:9]1[S:10][CH:11]=[CH:12][CH:13]=1.ClC1C=C(C=CC=1)C(OO)=[O:19]>C(Cl)Cl>[S:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:3]1[N:2]([CH3:1])[C:6]([S:7]([CH3:8])=[O:19])=[N:5][N:4]=1

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 6110894H-1,2,4-Triazole, 4-methyl-3-(methylthio)-5-(2-thienyl)-

Produkt 1

HCID 30880014H-1,2,4-Triazole, 4-methyl-3-(methylsulfinyl)-5-(2-thienyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred, 0° C., solution of 4-methyl-5-methylthio-3-(2-thienyl)-4H-1,2,4-triazole (4.85 g, 2.29×10-2 mole) and CH2Cl2 (170 ml) was added portionwise m-chloroperoxybenzoic acid (4.95 g, 2.29×10-2 mole). After stirring at room temperature overnight the reaction was washed two times with saturated aqueous NaHCO3 and one time with saturated aqueous NaCl, and dried over anhydrous N2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure yielding an off-white solid which was purified by flash chromatography (40% acetone/EtOAc). Crystallization from EtOAc afforded small colorless plates: 2.78 g (53%), mp 105°-107° C.

Aufarbeitung

  1. washwas washed two times with saturated aqueous NaHCO3 and one time with saturated aqueous NaCl
  2. customdried over anhydrous N2SO4
  3. customThe drying agent was removed by filtration
  4. customthe filtrate was evaporated at reduced pressure
  5. customyielding an off-white solid which
  6. customwas purified by flash chromatography (40% acetone/EtOAc)
  7. customCrystallization from EtOAc afforded small colorless plates

Quellen und Nachweise

ORD-Eintrag
ord-dc97481fa9ec4fe18d3199dc6192a7d2
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04900743

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