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2-Chloromethyl-4-(2-furylmethylthio)-3-methylpyridine hydrochloride → 2-{[[4-(2-Furylmethylthio)-3-methyl-2-pyridinyl]methyl]thio}-1H-benzimidazole

HRID 1081667
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1081667
Cl.Cl[CH2:3][C:4]1[C:9]([CH3:10])=[C:8]([S:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)[CH:7]=[CH:6][N:5]=1.[SH:18][C:19]1[NH:23][C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[N:20]=1>C(O)C.[OH-].[Na+]>[O:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[CH2:12][S:11][C:8]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:3][S:18][C:19]2[NH:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[N:20]=2)[C:9]=1[CH3:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 224607712-Chloromethyl-4-(2-furylmethylthio)-3-methylpyridine hydrochlorideHCID 178527775HCID 178527775, Verbindung

Produkt 1

HCID 97993662-{[[4-(2-Furylmethylthio)-3-methyl-2-pyridinyl]methyl]thio}-1H-benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

One equivalent (2.92 g) of 2-chloromethyl-4-(2-furylmethylthio)-3-methylpyridine hydrochloride (dissolved in 10 ml of water) is added dropwise at 40° C. in the course of 20 minutes to a solution of 2-mercapto-1H-benzimidazole (1.5 g/10 mmol) in 40 ml of ethanol and 21 ml of 1N sodium hydroxide solution. The mixture is subsequently stirred at 50°-60° C. for 2-3 h and at RT for a further 3-4 h, ethanol is distilled off on a rotary evaporator (1 kPa/40° C.), the residue is extracted 3 times using in each case 20 ml of dichloromethane, and the dichloromethane phase is washed with 0.1N sodium hydroxide solution, dried over potassium carbonate and evaporated fully in vacuo. For purification, the crude product is chromatographed on silica gel (dichloromethane/methanol 20:1 to 3:1); the collected pure fractions are together concentrated in vacuo and crystallized from dichloromethane/diisopropyl ether. The product is subsequently recrystallized from methanol/toluene. Yield: 2.61 g (71%) of the title compound as a colorless solid of m.p. 188°-189° C.

Aufarbeitung

  1. distillationethanol is distilled off on a rotary evaporator (1 kPa/40° C.)
  2. extractionthe residue is extracted 3 times
  3. washthe dichloromethane phase is washed with 0.1N sodium hydroxide solution
  4. dry with materialdried over potassium carbonate
  5. customevaporated fully in vacuo
  6. customFor purification
  7. customthe crude product is chromatographed on silica gel (dichloromethane/methanol 20:1 to 3:1)
  8. concentrationthe collected pure fractions are together concentrated in vacuo
  9. customcrystallized from dichloromethane/diisopropyl ether
  10. customThe product is subsequently recrystallized from methanol/toluene

Quellen und Nachweise

ORD-Eintrag
ord-0ef9df0804f648ac9878779c45229995
Quelldatensatz
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05587389

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