Methyl iodide → 4H-1,2,4-Triazole, 4-methyl-3-(methylthio)-5-(2-thienyl)-

HRID 1199379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1199379
[CH3:1]I.[CH3:3][N:4]1[C:8]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[N:7][NH:6][C:5]1=[S:14].[OH-].[Na+]>C(O)C>[S:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:8]1[N:4]([CH3:3])[C:5]([S:14][CH3:1])=[N:6][N:7]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 7219264-Methyl-5-(thiophen-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of methyl iodide (6.3 ml, 1.0×10-1 mole) in ethanol (32 ml) was added dropwise to a stirred, room temperature solution of 2,4-dihydro-4-methyl-5-(2-thienyl)-3H-1,2,4-triazole-3-thione (12.5 g, 6.34×10-2 mole) and 1 molar aqueous NaOH (142 ml, 1.42×10-1 mole). After being stirred for about 14 hours the reaction was extracted four times with EtOAc. The EtOAc extracts were combined, washed with saturated aqueous NaCl, and dried over anhydrous Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure giving a tacky yellow solid which was purified by flash chromatography (EtOAc). Crystallization from EtOAc gave colorless crystals: 10.5 g (78%), mp 83°-85° C.

Aufarbeitung

  1. extractionwas extracted four times with EtOAc
  2. washwashed with saturated aqueous NaCl
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe drying agent was removed by filtration
  5. customthe filtrate was evaporated at reduced pressure
  6. customgiving a tacky yellow solid which
  7. customwas purified by flash chromatography (EtOAc)
  8. customCrystallization from EtOAc
  9. customgave colorless crystals

Quellen und Nachweise

ORD-Eintrag
ord-3f86df03fbc44b5a9dbbe79c5c59b5d2
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04900743

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