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2-Chloromethyl-3-methyl-4-{4-[2-(2-methyl-5-nitroimidazol-1-yl)ethylthio]butylthio}pyridine → 2-(3-Methyl-4-{4-[2-(2-methyl-5-nitroimidazol-1-yl)ethylthio]butylthio}pyridin-2-ylmethylthio)-1 H-benzimidazole

HRID 342634
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 342634
Cl[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15][CH2:16][CH2:17][N:18]2[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=[C:19]2[CH3:26])[CH:6]=[CH:5][N:4]=1.[SH:27][C:28]1[NH:29][C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=1>C(O)(C)C>[CH3:9][C:8]1[C:3]([CH2:2][S:27][C:28]2[NH:32][C:31]3[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=3[N:29]=2)=[N:4][CH:5]=[CH:6][C:7]=1[S:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15][CH2:16][CH2:17][N:18]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=[C:19]1[CH3:26]
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Komponenten

4

Edukt 2

HCID 544598052-Chloromethyl-3-methyl-4-{4-[2-(2-methyl-5-nitroimidazol-1-yl)ethylthio]butylthio}pyridineHCID 178527775HCID 178527775, Verbindung

Produkt 1

HCID 675769092-(3-Methyl-4-{4-[2-(2-methyl-5-nitroimidazol-1-yl)ethylthio]butylthio}pyridin-2-ylmethylthio)-1 H-benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

2.5 g (6 mmol) of 2-chloromethyl-3-methyl-4-{4-[2-(2-methyl-5-nitroimidazol-1-yl)ethylthio]butylthio}-pyridine and 0.9 g (6 mmol) of 2-mercaptobenzimidazole are heated to reflux for 1 h in 25 ml of isopropanol. The mixture is then cooled in an ice bath and the precipitated solid is filtered off with suction. The solid is taken up in water and treated with saturated sodium hydrogen carbonate solution. The mixture is extracted with dichloromethane. The organic phase is washed with water, dried over magnesium sulfate, filtered and concentrated. The title compound crystallizes and is washed with a little methanol with stirring. M.p. 160°-162° C.; yield 0.62 g (20% of theory).

Aufarbeitung

  1. temperatureThe mixture is then cooled in an ice bath
  2. filtrationthe precipitated solid is filtered off with suction
  3. additiontreated with saturated sodium hydrogen carbonate solution
  4. extractionThe mixture is extracted with dichloromethane
  5. washThe organic phase is washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe title compound crystallizes
  10. washis washed with a little methanol

Quellen und Nachweise

ORD-Eintrag
ord-f8bb65aee53e47c5a9ac51b7bba0175a
Quelldatensatz
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05859030

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