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

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Reaction Steps

To a suspension of 1,2,3-triazol-4-thiol sodium salt (109 g : 870 mMol.) in dimethylformamide (300 ml) is added dropwise at -20° to -30° C. chloromethyl thiolacetate (109 g : 870 mMol.), and the mixture is stirred at room temperature for 2 hours. To the reaction mixture are added under ice cooling trityl chloride (292 g; 1.05 Mol.) and pyridine (84.6 ml : 1.05 Mol.), and the mixture is stirred at room temperature for 18 hours, diluted with dichloromethane, washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue is crystallized from ether to give 4-acetylthiomethylthio-1-trityl-1,2,3-triazole (183 g). Yield: 49%. mp. 115° to 116° C. Colorless crystals.

Provenance & Evidence