Cyclohexylamine → 2-(2-Cyclohexylamino-5-thiadiazolyl)-1-methyl-5nitroimidazole

HRID 462238

Reaktionsgleichung

Reaktionsgleichung von HRID 462238
Cl[N:2]1[NH:6][CH:5]=[C:4]([C:7]2[N:8]([CH3:15])[C:9]([N+:12]([O-:14])=[O:13])=[CH:10][N:11]=2)[S:3]1.[CH:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>O1CCOCC1>[CH:16]1([NH:22][N:2]2[NH:6][CH:5]=[C:4]([C:7]3[N:8]([CH3:15])[C:9]([N+:12]([O-:14])=[O:13])=[CH:10][N:11]=3)[S:3]2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Komponenten

4

Edukt 2

HCID 7965CyclohexylamineHCID 213908012-(2-Chloro-5-thiadiazolyl)-1-methyl-5-nitroimidazole

Produkt 1

HCID 213908612-(2-Cyclohexylamino-5-thiadiazolyl)-1-methyl-5nitroimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 5.0 g. of 2-(2-chloro-5-thiadiazolyl)-1-methyl-5-nitroimidazole, 6.0 g. of cyclohexylamine and 125 ml. of dioxane is stirred at reflux until thin-layer chromatographic analysis indicates that the chloro intermediate is completely utilized. The dioxane is removed under reduced pressure and the residue triturated with aqueous sodium bicarbonate solution. Recrystallization from a mixture of ethylacetate and acetone yields the pure compound melting at 215°-217° C.

Aufarbeitung

  1. additionA mixture of 5.0 g
  2. temperatureat reflux until thin-layer chromatographic analysis
  3. customThe dioxane is removed under reduced pressure
  4. customthe residue triturated with aqueous sodium bicarbonate solution
  5. customRecrystallization
  6. additionfrom a mixture of ethylacetate and acetone

Quellen und Nachweise

ORD-Eintrag
ord-adcb9dcdcc804a23b2b12019b726ef8a
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04065567

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