Sodium Iodide → HCID 18963346, compound

Participants

Reaction Steps

To a solution of 1-trityl-1,2,3-triazol-4-ylmethanol (8.00 g: 23.5 mMol.) in a mixture of dichloromethane (150 ml) and dimethylformamide (15 ml) at -40° C. are added triethylamine (3.9 ml: 28.0 mMol.) and methanesulfonyl chloride (2.2 ml: 28.4 mMol.), and the mixture is stirred at -30° to -40° C. for 25 minutes. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with brine, dried over sodium sulfate, and concentrated. To a solution of the residue in acetone (150 ml) are added potassium thiol-acetate (4.02 g: 35.2 mMol.) and sodium iodide (7.03 g: 46.9 mMol.), and the mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with water and brine, dried over sodium sulfate, and concentrated. The resulting crystals are washed with ether to give 4-acetylthioacetylthiomethyl- 1-trityl-1,2,3-triazole (8.01 g) as white crystals. Yield: 86%. mp. 172° to 173° C.

Provenance & Evidence