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Pyridine → 3-Acetylthiomethylthio-1-trityl-1,2,4-triazole

HRID 249577
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 249577
[NH:1]1[CH:5]=[N:4][C:3]([SH:6])=[N:2]1.[H-].[Na+].[S:9]1[CH:13]=C[CH:11]=[C:10]1CC(OCCl)=O.[C:20](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1C=CC=CC=1.CN(C)C=[O:49]>O>[C:10]([S:9][CH2:13][S:6][C:3]1[N:4]=[CH:5][N:1]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:2]=1)(=[O:49])[CH3:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 6

HCID 1049PyridineHCID 6228Dimethylformamide2×HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 57186933Chloromethyl thiolacetateHCID 178527894HCID 178527894, Verbindung

Produkt 1

HCID 10094304
3-Acetylthiomethylthio-1-trityl-1,2,4-triazole
Ausbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 1,2,4-triazole-3-thiol (2.23 g : 22.1 mMol.) in dimethylformamide (30 ml) is added sodium hydride (60% in oil : 840 mg : 21 mMol.), and the mixture is stirred at room temperature for 10 minutes. To this solution at -50° to -60° C. is added a solution of chloromethyl thiolacetate (2.50 g : 20.1 mMol.) in dimethylformamide (5 ml), and the mixture is stirred at the same temperature for 20 minutes, mixed with another trityl chloride (6.70 g : 24 mMol.) and pyridine (1.94 ml : 24.0 mMol.), stirred under ice cooling for 28 hours, diluted with water, and extracted with ethyl acetate. The extract is washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel chromatography (toluene : ethyl acetate=20: 1) and crystallized from ether to give 3- acetylthiomethylthio-1-trityl-1,2,4-triazole (3.37 g). Yield: 39%. Colorless crystals, mp. 124° to 125° C.

Aufarbeitung

  1. stirringthe mixture is stirred at the same temperature for 20 minutes
  2. stirringstirred under ice cooling for 28 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel chromatography (toluene : ethyl acetate=20: 1)
  8. customcrystallized from ether

Quellen und Nachweise

ORD-Eintrag
ord-67ed221eae5f46d6be57cfb93f394733
Quelldatensatz
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05214037

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